933:
542:
662:
994:
948:
613:
1018:
979:
964:
492:
404:
756:
625:
31:
642:
react with base to give epoxides. The reaction is spontaneous because the energetic cost of introducing the ring strain (13 kcal/mol) is offset by the larger bond enthalpy of the newly introduced C-O bond (when compared to that of the cleaved C-halogen bond).
646:
Formation of epoxides from secondary halohydrins is predicted to occur faster than from primary halohydrins due to increased entropic effects in the secondary halohydrin, and tertiary halohydrins react (if at all) extremely slowly due to steric crowding.
765:
Epoxides react with a broad range of nucleophiles, for example, alcohols, water, amines, thiols, and even halides. With two often-nearly-equivalent sites of attack, epoxides exemplify "ambident substrates". Ring-opening
366:
2137:
Niederer, Christian; Behra, Renata; Harder, Angela; Schwarzenbach, René P.; Escher, Beate I. (2004). "Mechanistic approaches for evaluating the toxicity of reactive organochlorines and epoxides in green algae".
993:
212:
catalysts are typically employed. According to a reaction mechanism suggested in 1974 at least one ethylene molecule is totally oxidized for every six that are converted to ethylene oxide:
984:
444:
Peroxycarboxylic acids, which are more electrophilic than other peroxides, convert alkenes to epoxides without the intervention of metal catalysts. In specialized applications,
185:
hydroperoxide can be used as oxygen sources during propylene oxidation (although a catalyst is required as well, and most industrial producers use dehydrochlorination instead).
932:
1296:
Nijhuis, T. Alexander; Makkee, Michiel; Moulijn, Jacob A.; Weckhuysen, Bert M. (1 May 2006). "The
Production of Propene Oxide: Catalytic Processes and Recent Developments".
1368:
Thiel W. R. (1997). "Metal catalyzed oxidations. Part 5. Catalytic olefin epoxidation with seven-coordinate oxobisperoxo molybdenum complexes: a mechanistic study".
398:(TBHP). Association of TBHP with the metal (M) generates the active metal peroxy complex containing the MOOR group, which then transfers an O center to the alkene.
978:
774:
2 pattern of attack at the least-substituted carbon, but can be affected by carbocation stability under acidic conditions. This class of reactions is the basis of
1882:
Bruce
Rickborn and Wallace E. Lamke (1967). "Reduction of epoxides. II. The lithium aluminum hydride and mixed hydride reduction of 3-methylcyclohexene oxide".
2082:; Martha A. Umbreit; Marjorie T. Nieh; Thomas C. Flood (1972). "Lower valent tungsten halides. New class of reagents for deoxygenation of organic molecules".
947:
556:
Chiral epoxides can often be derived enantioselectively from prochiral alkenes. Many metal complexes give active catalysts, but the most important involve
541:
510:
may be formed. In addition, if there are other stereocenters present in the starting material, they can influence the stereochemistry of the epoxidation.
215:
1982:
B. Mudryk; T. Cohen (1995). "1,3-Diols From
Lithium Β-lithioalkoxides Generated By The Reductive Lithiation Of Epoxides: 2,5-dimethyl-2,4-hexanediol".
498:
The stereochemistry of the reaction is quite sensitive. Depending on the mechanism of the reaction and the geometry of the alkene starting material,
70:, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and
1190:
1155:
2009:
Takuya
Nakagiri; Masahito Murai; Kazuhiko Takai (2015). "Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis".
1710:"Computational insights into the spontaneity of epoxide formation from halohydrins and other mechanistic details of Williamson's ether synthesis"
436:
to give a stabilized carbanion. This carbanion then attacks the same oxygen atom, displacing a leaving group from it, to close the epoxide ring.
1225:
Dietmar
Kahlich, Uwe Wiechern, Jörg Lindner "Propylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry, 2002 by Wiley-VCH, Weinheim.
1947:(2016). "Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships".
1017:
432:
can be epoxidized using nucleophilic oxygen compounds such as peroxides. The reaction is a two-step mechanism. First the oxygen performs a
114:
O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide
2199:
174:. Safety considerations weigh on these reactions because organic peroxides are prone to spontaneous decomposition or even combustion.
3118:
676:
90:
can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of
3123:
1627:
1682:"(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane"
1830:
1799:
1123:
1927:
1664:
1207:
1172:
963:
532:π electrons to attack. Because two bonds are broken and formed to the epoxide oxygen, this is formally an example of a
1341:
Indictor N., Brill W. F. (1965). "Metal
Acetylacetonate Catalyzed Epoxidation of Olefins with t-Butyl Hydroperoxide".
1422:
1089:
2192:
1269:
Kilty P. A.; Sachtler W. M. H. (1974). "The mechanism of the selective oxidation of ethylene to ethylene oxide".
433:
1555:
Sheldon R. A. (1980). "Synthetic and mechanistic aspects of metal-catalysed epoxidations with hydroperoxides".
1242:
Sajkowski, D. J.; Boudart, M. (1987). "Structure
Sensitivity of the Catalytic Oxidation of Ethene by Silver".
3022:
468:
513:
The reaction proceeds via what is commonly known as the "Butterfly
Mechanism". The peroxide is viewed as an
1046:
938:
1820:
1103:
453:
17:
3151:
2595:
2185:
708:
704:
521:. The reaction is considered to be concerted. The butterfly mechanism allows ideal positioning of the
1396:
781:
2632:
700:
395:
2078:
901:
Epoxides undergo ring expansion reactions, illustrated by the insertion of carbon dioxide to give
3105:
491:
206:
163:, which are produced respectively on the scales of approximately 15 and 3 million tonnes/year.
816:, also known as polyethylene oxide. The reaction of an alcohol or a phenol with ethylene oxide,
695:
Epoxides are uncommon in nature. They arise usually via oxygenation of alkenes by the action of
3005:
1004:
792:
epoxides through a simple nucleophilic addition of hydride (H); they produce the corresponding
651:
75:
67:
3112:
3000:
867:
595:
576:
407:
Simplified mechanism for metal-catalyzed epoxidation of alkenes with peroxide (ROOH) reagents
371:
178:
661:
3081:
2526:
2079:
2047:, Martha A. Umbreit (1981). "Deoxygenation of Epoxides with Lower Valent Tungsten Halides:
1057:
580:
2110:
Sasaki, Hiroshi (February 2007). "Curing properties of cycloaliphatic epoxy derivatives".
8:
2387:
909:
813:
793:
460:
2163:
2044:
1944:
1767:
1742:
1614:
1583:
1323:
1115:
533:
413:
144:
1624:
1528:
Berrisford, D. J.; Bolm, C.; Sharpless, K. B. (2003). "Ligand-Accelerated
Catalysis".
1381:
3146:
3071:
3041:
2799:
2421:
2155:
2084:
2026:
1964:
1923:
1826:
1795:
1772:
1686:
1660:
1588:
1568:
1472:
1418:
1203:
1168:
1119:
1084:
789:
785:
602:
525:
449:
391:
39:
1864:
1327:
587:, these reactions are useful for the enantioselective synthesis of chiral epoxides.
2776:
2270:
2208:
2147:
2123:
2119:
2092:
2061:
2018:
1991:
1956:
1915:
1892:
1762:
1754:
1721:
1652:
1596:
1564:
1537:
1448:
1377:
1350:
1313:
1305:
1278:
1251:
1226:
1195:
1160:
1111:
1072:
767:
669:
572:
115:
87:
51:
2167:
1656:
2995:
2754:
2749:
2732:
2715:
2516:
2265:
1631:
1042:
902:
718:
696:
684:
655:
631:, is prepared by the chlorohydrin method. It is a precursor in the production of
628:
584:
479:
394:
and alkyl hydroperoxides. Metal-catalyzed epoxidations were first explored using
160:
2022:
1960:
1942:
1681:
1494:
Paul D. Bartlett (1950). "Recent work on the mechanisms of peroxide reactions".
1467:
3066:
3061:
2937:
2932:
2927:
2720:
2687:
2471:
2453:
2443:
1034:
871:
809:
194:
156:
103:
1452:
1282:
1255:
3140:
3086:
3034:
2965:
2851:
2841:
2836:
2826:
2821:
2771:
2766:
2682:
2677:
2667:
2521:
2476:
2438:
2426:
2397:
2275:
2065:
1995:
1919:
1910:
Kosswig, Kurt (2002). "Surfactants". In Elvers, Barbara; et al. (eds.).
1884:
1230:
1199:
1164:
1023:
606:
483:
1439:[Oxidation of unsaturated compounds by means of organic peroxides].
668:
An intramolecular epoxide formation reaction is one of the key steps in the
3017:
2904:
2899:
2876:
2627:
2466:
2392:
2329:
2324:
2302:
2258:
2243:
2233:
2159:
2030:
2008:
1968:
1776:
1726:
1709:
1541:
1038:
817:
612:
514:
507:
429:
182:
1743:"Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis"
1152:
687:. In this reaction, a sulfonium is the leaving group instead of chloride.
3076:
3029:
2990:
2871:
2759:
2744:
2739:
2727:
2292:
2287:
2253:
2248:
2238:
2216:
2053:
1860:
1816:
1619:
1008:
734:
722:
714:
632:
588:
518:
63:
2096:
1896:
1600:
1354:
2985:
2976:
2856:
2811:
2707:
2672:
2662:
2602:
2538:
2461:
2409:
1052:
The reaction of epoxides with amines is the basis for the formation of
969:
889:
856:
639:
599:
565:
464:
1758:
1318:
1309:
866:
reagents, with loss or retention of configuration. The combination of
416:
catalyzes the epoxidation at specifically less-substituted alkenes.
361:{\displaystyle {\ce {7 H2C=CH2 + 6 O2 -> 6 C2H4O + 2 CO2 + 2 H2O}}}
2952:
2866:
2831:
2816:
2804:
2647:
2622:
2431:
2043:
1437:"Oxydation ungesättigter Verbindungen mittels organischer Superoxyde"
863:
805:
755:
605:. It is used to prepare 2,3-epoxyalcohols from primary and secondary
445:
403:
375:
2177:
1436:
2960:
2914:
2881:
2577:
2483:
2357:
2312:
2297:
1881:
1000:
954:
885:
730:
680:
624:
561:
557:
198:
167:
91:
71:
2151:
30:
2922:
2846:
2697:
2692:
2657:
2642:
2637:
2607:
2590:
2341:
2307:
1586:(1980). "The first practical method for asymmetric epoxidation".
726:
475:
130:
2136:
1822:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
1153:
Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides".
545:
The butterfly mechanism for the Prilezhaev epoxidation reaction.
390:
Metal complexes are useful catalysts for epoxidations involving
3010:
2942:
2786:
2495:
2488:
2382:
2363:
2352:
2336:
2282:
1465:
1415:
Advanced Organic Chemistry, Reactions, Mechanisms and Structure
878:
737:), the epoxides are often obtained in high enantioselectivity.
619:
209:
202:
171:
59:
55:
1295:
2891:
2861:
2794:
2652:
2617:
2612:
2585:
2533:
2500:
2404:
2228:
1865:"How to predict the regioselectivity of epoxide ring opening"
1814:
1053:
775:
591:
reagents may also be used to generate epoxides from alkenes.
425:
140:
135:
47:
1268:
1056:
glues and structural materials. A typical amine-hardener is
985:
3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate
745:
Ring-opening reactions dominate the reactivity of epoxides.
463:. This approach involves the oxidation of the alkene with a
166:
Aside from ethylene oxide, most epoxides are generated when
2319:
1825:(6th ed.), New York: Wiley-Interscience, p. 517,
1679:
1581:
379:
748:
1187:
1037:
is widely used to generate detergents and surfactants by
351:
331:
308:
295:
275:
255:
234:
1340:
385:
1647:
Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins".
1623:, Coll. Vol. 7, p. 461 (1990); Vol. 63, p. 66 (1985). (
1527:
439:
1792:
Medical Physiology: A Cellular And Molecular Approach
1434:
799:
218:
1106:. In Craver, Clara D.; Carraher, Charles E. (eds.).
1909:
1188:Siegfried Rebsdat; Dieter Mayer. "Ethylene Oxide".
908:An epoxide adjacent to an alcohol can undergo the
360:
27:Organic compounds with a carbon-carbon-oxygen ring
1981:
1642:
1640:
139:. However, few if any of the epoxy groups in the
3138:
1740:
1673:
1493:
1241:
851:
717:are intermediates in the oxidation of arenes by
197:industry generates its product from reaction of
1512:
1298:Industrial & Engineering Chemistry Research
1101:
703:which act as signalling molecules. and similar
382:catalysts can selectively epoxidize propylene.
1912:Ullmann's Encyclopedia of Industrial Chemistry
1649:Ullmann's Encyclopedia of Industrial Chemistry
1637:
1441:Berichte der Deutschen Chemischen Gesellschaft
1191:Ullmann's Encyclopedia of Industrial Chemistry
1156:Ullmann's Encyclopedia of Industrial Chemistry
1146:
1102:Massingill, J. L.; Bauer, R. S. (2000-01-01).
770:in asymmetric epoxides generally follows the S
571:Hydroperoxides are also employed in catalytic
2193:
1847:Organic Synthesis: the disconnection approach
1783:
1554:
1026:exists in equilibrium with the oxepin isomer.
759:Two pathways for the hydrolysis of an epoxide
374:. Other alkenes fail to react usefully, even
62:. This triangular structure has substantial
660:
620:Dehydrohalogenation and other γ eliminations
611:
133:formed from epoxide precursors is called an
2103:
1903:
1844:
1707:
1575:
1367:
941:is a component in common household "epoxy".
848:With anhydrides, epoxides give polyesters.
419:
170:reagents donate a single oxygen atom to an
2200:
2186:
1517:. Interscience, New York. pp. 67–106.
1459:
1370:Journal of Molecular Catalysis A: Chemical
1271:Catalysis Reviews: Science and Engineering
551:
1766:
1725:
1646:
1317:
820:, is widely used to produce surfactants:
459:Typical laboratory operations employ the
370:Only ethylene produces an epoxide during
340:
320:
284:
264:
223:
1466:Harold Hibbert and Pauline Burt (1941).
754:
623:
402:
29:
859:cleaves the ring to β-lithioalkoxides.
749:Hydrolysis and addition of nucleophiles
155:The dominant epoxides industrially are
14:
3139:
2140:Environmental Toxicology and Chemistry
2109:
1680:Koppenhoefer, B.; Schurig, V. (1993).
1110:. Oxford: Pergamon. pp. 393–424.
1049:of medical instruments and materials.
953:The chemical structure of the epoxide
2207:
2181:
1859:
1789:
1548:
1407:
1394:
1108:Applied Polymer Science: 21st Century
778:glues and the production of glycols.
474:. Illustrative is the epoxidation of
386:Organic peroxides and metal catalysts
188:
50:, where the ether forms a three-atom
1845:Warren, Stuart; Wyatt, Paul (2008).
1334:
1262:
1221:
1219:
1075:, making many of them highly toxic.
440:Transfer from peroxycarboxylic acids
424:Electron-deficient olefins, such as
862:Epoxides can be deoxygenated using
24:
1943:Julie M. Longo; Maria J. Sanford;
1849:(2nd ed.). Wiley. p. 39.
1794:. Elsevier/Saunders. p. 108.
1095:
895:
800:Polymerization and oligomerization
540:
86:A compound containing the epoxide
25:
3163:
1417:. 3rd ed. John Wiley & Sons.
1216:
1007:(ESBO), a commercially important
972:are naturally occurring epoxides.
957:, a common chemical intermediate.
804:Polymerization of epoxides gives
677:Johnson–Corey–Chaykovsky reaction
1397:"Selective reactions of Alkenes"
1116:10.1016/b978-008043417-9/50023-4
1016:
992:
977:
962:
946:
931:
699:. (but see also the short-lived
654:, most of the world's supply of
490:
2130:
2072:
2037:
2002:
1975:
1936:
1875:
1853:
1838:
1808:
1734:
1701:
1607:
1521:
1506:
1487:
1428:
1395:Taber, Douglass (25 Sep 2006).
690:
598:reaction is one of the premier
434:nucleophilic conjugate addition
81:
2124:10.1016/j.porgcoat.2006.09.030
1557:Journal of Molecular Catalysis
1435:Nikolaus Prileschajew (1909).
1388:
1361:
1289:
1235:
1181:
278:
13:
1:
1657:10.1002/14356007.a09_547.pub2
1382:10.1016/S1381-1169(96)00291-9
1139:
852:Metallation and deoxygenation
2112:Progress in Organic Coatings
1914:. Weinheim, GER: Wiley-VCH.
1569:10.1016/0304-5102(80)85010-3
1515:Peroxide Reaction Mechanisms
1401:Organic Chemistry Highlights
939:Bisphenol A diglycidyl ether
740:
679:epoxides are generated from
456:, but are more explosive.
150:
7:
2023:10.1021/acs.orglett.5b01583
1961:10.1021/acs.chemrev.6b00553
1617:; Exon, C. M.; Regenye, R.
1496:Record of Chemical Progress
1078:
709:epoxyeicosatetraenoic acids
705:epoxydocosapentaenoic acids
122:, which can also be called
10:
3168:
1696:, vol. 8, p. 434
1530:Angew. Chem. Int. Ed. Engl
1482:, vol. 1, p. 494
888:, epoxides convert to the
575:epoxidations, such as the
534:coarctate transition state
3095:
3054:
2974:
2951:
2913:
2890:
2785:
2706:
2576:
2553:
2509:
2452:
2375:
2350:
2215:
1741:Thibodeaux C. J. (2012).
1453:10.1002/cber.190904204100
1283:10.1080/01614947408079624
1256:10.1080/01614948708078611
1090:Juliá–Colonna epoxidation
1066:
1041:. Its hydrolysis affords
782:Lithium aluminium hydride
701:epoxyeicosatrienoic acids
658:arises via this route.
66:, making epoxides highly
2066:10.15227/orgsyn.060.0029
1996:10.15227/orgsyn.072.0173
1920:10.1002/14356007.a25_747
1513:John O. Edwards (1962).
1231:10.1002/14356007.a22_239
1200:10.1002/14356007.a10_117
1165:10.1002/14356007.a09_531
987:, precursor to coatings.
721:. For prochiral arenes (
420:Nucleophilic epoxidation
396:tert-butyl hydroperoxide
378:, though TS-1 supported
3106:chemical classification
1194:. Weinheim: Wiley-VCH.
1159:. Weinheim: Wiley-VCH.
1003:, a major component of
916:
552:Asymmetric epoxidations
1869:Chemistry with a twist
1727:10.19261/cjm.2023.1083
1542:10.1002/anie.199510591
1045:. It is also used for
1005:epoxidized soybean oil
760:
665:
652:propylene chlorohydrin
636:
616:
546:
408:
362:
35:
3113:chemical nomenclature
923:Illustrative epoxides
868:tungsten hexachloride
758:
664:
627:
615:
596:Sharpless epoxidation
577:Sharpless epoxidation
544:
406:
372:incomplete combustion
363:
179:t-butyl hydroperoxide
118:, as in the compound
33:
1708:Silva, P.J. (2023).
1413:March, Jerry. 1985.
1058:triethylenetetramine
812:polymerizes to give
583:. Together with the
581:Jacobsen epoxidation
216:
2569:not C, H or O)
2097:10.1021/ja00773a045
1955:(24): 15167–15197.
1897:10.1021/jo01278a005
1815:Smith, Michael B.;
1601:10.1021/ja00538a077
1355:10.1021/jo01017a520
910:Payne rearrangement
814:polyethylene glycol
517:, and the alkene a
461:Prilezhaev reaction
353:
333:
310:
297:
277:
257:
236:
3011:Hypervalent iodine
2080:K. Barry Sharpless
2045:K. Barry Sharpless
1945:Geoffrey W. Coates
1630:2013-09-27 at the
884:When treated with
761:
666:
637:
617:
603:chemical reactions
547:
526:sigma star orbital
414:Vanadium(II) oxide
409:
358:
341:
321:
298:
285:
265:
245:
224:
189:Ethylene oxidation
36:
3152:Functional groups
3134:
3133:
3072:Sulfenyl chloride
3050:
3049:
2549:
2548:
2368:(only C, H and O)
2209:Functional groups
2091:(18): 6538–6540.
2085:J. Am. Chem. Soc.
2051:-Cyclododecene".
1863:(28 April 2013).
1832:978-0-471-72091-1
1801:978-1-4160-2328-9
1790:Boron WF (2003).
1759:10.1021/cr200073d
1694:Collected Volumes
1687:Organic Syntheses
1595:(18): 5974–5976.
1589:J. Am. Chem. Soc.
1536:(10): 1059–1070.
1480:Collected Volumes
1473:Organic Syntheses
1310:10.1021/ie0513090
1304:(10): 3447–3459.
1244:Catalysis Reviews
1125:978-0-08-043417-9
1085:Epoxide hydrolase
1073:alkylating agents
903:cyclic carbonates
786:aluminium hydride
454:perform similarly
450:dimethyldioxirane
430:acryl derivatives
392:hydrogen peroxide
356:
344:
324:
313:
301:
288:
268:
248:
239:
227:
124:1,2-heptene oxide
40:organic chemistry
34:A generic epoxide
16:(Redirected from
3159:
3101:
3006:Trifluoromethoxy
2574:
2573:
2570:
2373:
2372:
2369:
2222:
2202:
2195:
2188:
2179:
2178:
2172:
2171:
2134:
2128:
2127:
2118:(2–3): 227–230.
2107:
2101:
2100:
2076:
2070:
2069:
2041:
2035:
2034:
2006:
2000:
1999:
1979:
1973:
1972:
1940:
1934:
1933:
1907:
1901:
1900:
1879:
1873:
1872:
1857:
1851:
1850:
1842:
1836:
1835:
1812:
1806:
1805:
1787:
1781:
1780:
1770:
1753:(3): 1681–1709.
1738:
1732:
1731:
1729:
1705:
1699:
1697:
1690:
1677:
1671:
1670:
1644:
1635:
1615:Sharpless, K. B.
1611:
1605:
1604:
1584:Sharpless, K. B.
1579:
1573:
1572:
1552:
1546:
1545:
1525:
1519:
1518:
1510:
1504:
1503:
1491:
1485:
1483:
1476:
1463:
1457:
1456:
1447:(4): 4811–4815.
1432:
1426:
1411:
1405:
1404:
1392:
1386:
1385:
1365:
1359:
1358:
1338:
1332:
1331:
1321:
1293:
1287:
1286:
1266:
1260:
1259:
1239:
1233:
1223:
1214:
1213:
1185:
1179:
1178:
1150:
1135:
1133:
1132:
1020:
996:
981:
966:
950:
935:
768:regioselectivity
685:sulfonium ylides
670:Darzens reaction
607:allylic alcohols
600:enantioselective
573:enantioselective
531:
524:
494:
367:
365:
364:
359:
357:
354:
352:
349:
342:
332:
329:
322:
311:
309:
306:
299:
296:
293:
286:
276:
273:
266:
256:
253:
246:
244:
237:
235:
232:
225:
120:1,2-epoxyheptane
116:functional group
88:functional group
58:and one atom of
21:
3167:
3166:
3162:
3161:
3160:
3158:
3157:
3156:
3137:
3136:
3135:
3130:
3099:
3091:
3046:
3001:Trichloromethyl
2996:Trifluoromethyl
2970:
2947:
2909:
2886:
2781:
2750:Phosphine oxide
2702:
2568:
2566:
2565:
2563:
2561:
2559:
2557:
2555:
2545:
2505:
2448:
2367:
2366:
2361:
2356:
2346:
2220:
2219:
2211:
2206:
2176:
2175:
2135:
2131:
2108:
2104:
2077:
2073:
2042:
2038:
2007:
2003:
1980:
1976:
1941:
1937:
1930:
1908:
1904:
1880:
1876:
1858:
1854:
1843:
1839:
1833:
1813:
1809:
1802:
1788:
1784:
1739:
1735:
1706:
1702:
1692:
1678:
1674:
1667:
1645:
1638:
1632:Wayback Machine
1612:
1608:
1580:
1576:
1553:
1549:
1526:
1522:
1511:
1507:
1492:
1488:
1478:
1468:"Styrene Oxide"
1464:
1460:
1433:
1429:
1412:
1408:
1393:
1389:
1366:
1362:
1339:
1335:
1294:
1290:
1267:
1263:
1240:
1236:
1224:
1217:
1210:
1186:
1182:
1175:
1151:
1147:
1142:
1130:
1128:
1126:
1098:
1096:Further reading
1081:
1069:
1063:
1043:ethylene glycol
1032:
1031:
1030:
1027:
1021:
1012:
997:
988:
982:
973:
967:
958:
951:
942:
936:
925:
924:
919:
898:
896:Other reactions
854:
843:
839:
835:
831:
827:
802:
773:
751:
743:
719:cytochrome P450
697:cytochrome P450
693:
656:propylene oxide
629:Epichlorohydrin
622:
585:Shi epoxidation
554:
529:
522:
480:perbenzoic acid
448:reagents (e.g.
442:
422:
388:
350:
345:
330:
325:
307:
302:
294:
289:
274:
269:
254:
249:
240:
233:
228:
219:
217:
214:
213:
191:
161:propylene oxide
153:
113:
109:
101:
97:
84:
54:: two atoms of
28:
23:
22:
15:
12:
11:
5:
3165:
3155:
3154:
3149:
3132:
3131:
3129:
3128:
3127:
3126:
3121:
3109:
3102:
3096:
3093:
3092:
3090:
3089:
3087:Sulfinylamines
3084:
3079:
3074:
3069:
3067:Phosphoramides
3064:
3062:Isothiocyanate
3058:
3056:
3052:
3051:
3048:
3047:
3045:
3044:
3039:
3038:
3037:
3027:
3026:
3025:
3015:
3014:
3013:
3008:
3003:
2998:
2993:
2982:
2980:
2972:
2971:
2969:
2968:
2963:
2957:
2955:
2949:
2948:
2946:
2945:
2940:
2938:Selenenic acid
2935:
2933:Seleninic acid
2930:
2928:Selenonic acid
2925:
2919:
2917:
2911:
2910:
2908:
2907:
2902:
2896:
2894:
2888:
2887:
2885:
2884:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2808:
2807:
2797:
2791:
2789:
2783:
2782:
2780:
2779:
2774:
2769:
2764:
2763:
2762:
2752:
2747:
2742:
2737:
2736:
2735:
2725:
2724:
2723:
2721:Phosphodiester
2712:
2710:
2704:
2703:
2701:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2599:
2598:
2593:
2582:
2580:
2571:
2567:(one element,
2551:
2550:
2547:
2546:
2544:
2543:
2542:
2541:
2531:
2530:
2529:
2524:
2513:
2511:
2507:
2506:
2504:
2503:
2498:
2493:
2492:
2491:
2481:
2480:
2479:
2474:
2469:
2458:
2456:
2450:
2449:
2447:
2446:
2444:Methylenedioxy
2441:
2436:
2435:
2434:
2429:
2419:
2418:
2417:
2412:
2402:
2401:
2400:
2390:
2385:
2379:
2377:
2370:
2348:
2347:
2345:
2344:
2339:
2334:
2333:
2332:
2327:
2317:
2316:
2315:
2310:
2305:
2300:
2295:
2290:
2280:
2279:
2278:
2273:
2263:
2262:
2261:
2256:
2251:
2246:
2241:
2236:
2225:
2223:
2221:(only C and H)
2213:
2212:
2205:
2204:
2197:
2190:
2182:
2174:
2173:
2146:(3): 697–704.
2129:
2102:
2071:
2036:
2017:(13): 3346–9.
2001:
1974:
1935:
1929:978-3527306732
1928:
1902:
1891:(3): 537–539.
1874:
1852:
1837:
1831:
1807:
1800:
1782:
1733:
1700:
1672:
1666:978-3527306732
1665:
1636:
1606:
1574:
1547:
1520:
1505:
1486:
1458:
1427:
1406:
1387:
1360:
1333:
1288:
1261:
1250:(4): 325–360.
1234:
1215:
1209:978-3527306732
1208:
1180:
1174:978-3527306732
1173:
1144:
1143:
1141:
1138:
1137:
1136:
1124:
1104:"Epoxy Resins"
1097:
1094:
1093:
1092:
1087:
1080:
1077:
1068:
1065:
1035:Ethylene oxide
1029:
1028:
1022:
1015:
1013:
998:
991:
989:
983:
976:
974:
968:
961:
959:
952:
945:
943:
937:
930:
927:
926:
922:
921:
920:
918:
915:
914:
913:
906:
897:
894:
853:
850:
846:
845:
841:
837:
833:
829:
825:
810:ethylene oxide
808:. For example
801:
798:
771:
763:
762:
750:
747:
742:
739:
692:
689:
650:Starting with
621:
618:
553:
550:
549:
548:
496:
495:
441:
438:
421:
418:
411:
410:
387:
384:
348:
339:
336:
328:
319:
316:
305:
292:
283:
280:
272:
263:
260:
252:
243:
231:
222:
195:ethylene oxide
190:
187:
157:ethylene oxide
152:
149:
145:curing process
111:
107:
104:ethylene oxide
99:
95:
83:
80:
26:
9:
6:
4:
3:
2:
3164:
3153:
3150:
3148:
3145:
3144:
3142:
3125:
3122:
3120:
3117:
3116:
3115:
3114:
3110:
3108:
3107:
3103:
3098:
3097:
3094:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3059:
3057:
3053:
3043:
3040:
3036:
3033:
3032:
3031:
3028:
3024:
3021:
3020:
3019:
3016:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2988:
2987:
2984:
2983:
2981:
2979:
2978:
2973:
2967:
2966:Telluroketone
2964:
2962:
2959:
2958:
2956:
2954:
2950:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2920:
2918:
2916:
2912:
2906:
2903:
2901:
2898:
2897:
2895:
2893:
2889:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2852:Sulfonic acid
2850:
2848:
2845:
2843:
2842:Sulfinic acid
2840:
2838:
2837:Thiosulfonate
2835:
2833:
2830:
2828:
2827:Thiosulfinate
2825:
2823:
2822:Sulfenic acid
2820:
2818:
2815:
2813:
2810:
2806:
2803:
2802:
2801:
2798:
2796:
2793:
2792:
2790:
2788:
2784:
2778:
2777:Phosphaallene
2775:
2773:
2772:Phosphaalkyne
2770:
2768:
2767:Phosphaalkene
2765:
2761:
2758:
2757:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2734:
2731:
2730:
2729:
2726:
2722:
2719:
2718:
2717:
2714:
2713:
2711:
2709:
2705:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2597:
2594:
2592:
2589:
2588:
2587:
2584:
2583:
2581:
2579:
2575:
2572:
2552:
2540:
2537:
2536:
2535:
2532:
2528:
2525:
2523:
2520:
2519:
2518:
2515:
2514:
2512:
2508:
2502:
2499:
2497:
2494:
2490:
2487:
2486:
2485:
2482:
2478:
2475:
2473:
2470:
2468:
2465:
2464:
2463:
2460:
2459:
2457:
2455:
2451:
2445:
2442:
2440:
2439:Ethylenedioxy
2437:
2433:
2430:
2428:
2425:
2424:
2423:
2420:
2416:
2413:
2411:
2408:
2407:
2406:
2403:
2399:
2396:
2395:
2394:
2391:
2389:
2386:
2384:
2381:
2380:
2378:
2374:
2371:
2365:
2359:
2354:
2349:
2343:
2340:
2338:
2335:
2331:
2328:
2326:
2323:
2322:
2321:
2318:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2285:
2284:
2281:
2277:
2274:
2272:
2269:
2268:
2267:
2264:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2231:
2230:
2227:
2226:
2224:
2218:
2214:
2210:
2203:
2198:
2196:
2191:
2189:
2184:
2183:
2180:
2169:
2165:
2161:
2157:
2153:
2152:10.1897/03-83
2149:
2145:
2141:
2133:
2125:
2121:
2117:
2113:
2106:
2098:
2094:
2090:
2087:
2086:
2081:
2075:
2067:
2063:
2059:
2056:
2055:
2050:
2046:
2040:
2032:
2028:
2024:
2020:
2016:
2012:
2005:
1997:
1993:
1989:
1985:
1978:
1970:
1966:
1962:
1958:
1954:
1950:
1946:
1939:
1931:
1925:
1921:
1917:
1913:
1906:
1898:
1894:
1890:
1887:
1886:
1885:J. Org. Chem.
1878:
1870:
1866:
1862:
1856:
1848:
1841:
1834:
1828:
1824:
1823:
1818:
1811:
1803:
1797:
1793:
1786:
1778:
1774:
1769:
1764:
1760:
1756:
1752:
1748:
1744:
1737:
1728:
1723:
1719:
1715:
1714:Chem. J. Mold
1711:
1704:
1695:
1689:
1688:
1683:
1676:
1668:
1662:
1658:
1654:
1651:. Wiley-VCH.
1650:
1643:
1641:
1633:
1629:
1626:
1622:
1621:
1616:
1613:Hill, J. G.;
1610:
1602:
1598:
1594:
1591:
1590:
1585:
1582:Katsuki, T.;
1578:
1570:
1566:
1562:
1558:
1551:
1543:
1539:
1535:
1531:
1524:
1516:
1509:
1501:
1497:
1490:
1481:
1475:
1474:
1469:
1462:
1454:
1450:
1446:
1443:(in German).
1442:
1438:
1431:
1424:
1423:0-471-85472-7
1420:
1416:
1410:
1402:
1398:
1391:
1383:
1379:
1375:
1371:
1364:
1356:
1352:
1348:
1344:
1337:
1329:
1325:
1320:
1315:
1311:
1307:
1303:
1299:
1292:
1284:
1280:
1276:
1272:
1265:
1257:
1253:
1249:
1245:
1238:
1232:
1228:
1222:
1220:
1211:
1205:
1201:
1197:
1193:
1192:
1184:
1176:
1170:
1166:
1162:
1158:
1157:
1149:
1145:
1127:
1121:
1117:
1113:
1109:
1105:
1100:
1099:
1091:
1088:
1086:
1083:
1082:
1076:
1074:
1071:Epoxides are
1064:
1061:
1059:
1055:
1050:
1048:
1047:sterilisation
1044:
1040:
1036:
1025:
1024:Benzene oxide
1019:
1014:
1010:
1006:
1002:
995:
990:
986:
980:
975:
971:
965:
960:
956:
949:
944:
940:
934:
929:
928:
911:
907:
904:
900:
899:
893:
892:(thiiranes).
891:
887:
882:
880:
876:
875:-butyllithium
874:
869:
865:
860:
858:
849:
823:
822:
821:
819:
815:
811:
807:
797:
795:
791:
787:
783:
779:
777:
769:
757:
753:
752:
746:
738:
736:
732:
728:
724:
720:
716:
712:
710:
706:
702:
698:
688:
686:
682:
678:
673:
671:
663:
659:
657:
653:
648:
644:
641:
634:
630:
626:
614:
610:
608:
604:
601:
597:
592:
590:
586:
582:
578:
574:
569:
567:
563:
559:
543:
539:
538:
537:
535:
527:
520:
516:
511:
509:
508:diastereomers
505:
501:
493:
489:
488:
487:
485:
484:styrene oxide
481:
477:
473:
471:
466:
462:
457:
455:
451:
447:
437:
435:
431:
427:
417:
415:
405:
401:
400:
399:
397:
393:
383:
381:
377:
373:
368:
346:
337:
334:
326:
317:
314:
303:
290:
281:
270:
261:
258:
250:
241:
229:
220:
211:
208:
207:heterogeneous
204:
200:
196:
186:
184:
180:
175:
173:
169:
164:
162:
158:
148:
146:
142:
138:
137:
132:
127:
125:
121:
117:
105:
93:
89:
79:
77:
73:
69:
65:
61:
57:
53:
49:
45:
41:
32:
19:
3111:
3104:
3018:Vinyl halide
2975:
2905:Borinic acid
2900:Boronic acid
2877:Thioxanthate
2414:
2217:Hydrocarbons
2143:
2139:
2132:
2115:
2111:
2105:
2088:
2083:
2074:
2057:
2052:
2048:
2039:
2014:
2010:
2004:
1987:
1983:
1977:
1952:
1948:
1938:
1911:
1905:
1888:
1883:
1877:
1868:
1861:Rzepa, Henry
1855:
1846:
1840:
1821:
1817:March, Jerry
1810:
1791:
1785:
1750:
1746:
1736:
1720:(2): 87–95.
1717:
1713:
1703:
1693:
1685:
1675:
1648:
1618:
1609:
1592:
1587:
1577:
1560:
1556:
1550:
1533:
1529:
1523:
1514:
1508:
1499:
1495:
1489:
1479:
1471:
1461:
1444:
1440:
1430:
1414:
1409:
1400:
1390:
1373:
1369:
1363:
1346:
1343:J. Org. Chem
1342:
1336:
1301:
1297:
1291:
1274:
1270:
1264:
1247:
1243:
1237:
1189:
1183:
1154:
1148:
1129:. Retrieved
1107:
1070:
1062:
1051:
1039:ethoxylation
1033:
883:
872:
861:
855:
847:
832:O → R(OC
818:ethoxylation
803:
780:
764:
744:
715:Arene oxides
713:
694:
691:Biosynthesis
674:
667:
649:
645:
638:
633:epoxy resins
593:
570:
555:
515:electrophile
512:
503:
499:
497:
469:
458:
443:
423:
412:
389:
369:
192:
183:ethylbenzene
176:
165:
154:
143:survive the
134:
128:
123:
119:
85:
82:Nomenclature
74:, and often
46:is a cyclic
43:
37:
3082:Thiocyanate
3077:Sulfonamide
3042:Perchlorate
3030:Acyl halide
2991:Fluoroethyl
2872:Thionoester
2760:Phosphonium
2745:Phosphinate
2740:Phosphonous
2728:Phosphonate
2427:Hydroperoxy
2249:Cyclopropyl
2054:Org. Synth.
1620:Org. Synth.
1563:: 107–206.
1376:: 449–454.
1349:(6): 2074.
1009:plasticizer
999:Epoxidized
970:Epothilones
824:ROH + n C
735:benzopyrene
723:naphthalene
683:groups and
640:Halohydrins
589:Oxaziridine
519:nucleophile
205:. Modified
168:peroxidized
64:ring strain
18:Epoxidation
3141:Categories
2986:Haloalkane
2857:Thioketone
2812:Persulfide
2708:Phosphorus
2673:Isocyanate
2663:Isonitrile
2564:or oxygen
2562:hydrogen,
2558:not being
2539:Orthoester
2432:Dioxiranes
2410:Enol ether
2298:1-Propenyl
1984:Org. Synth
1319:1874/20149
1140:References
1131:2023-12-20
890:episulfide
877:gives the
857:Lithiation
806:polyethers
566:molybdenum
465:peroxyacid
3119:inorganic
2953:Tellurium
2867:Thioester
2832:Sulfoxide
2817:Disulfide
2805:Sulfonium
2755:Phosphine
2733:Phosphite
2716:Phosphate
2648:Carbamate
2623:Hydrazone
2556:element,
2554:Only one
2527:Anhydride
2266:Methylene
2011:Org. Lett
1949:Chem. Rev
1747:Chem. Rev
864:oxophilic
741:Reactions
731:benzoates
446:dioxirane
376:propylene
279:⟶
151:Synthesis
3147:Epoxides
3100:See also
3035:Chloride
2961:Tellurol
2915:Selenium
2882:Xanthate
2596:Ammonium
2578:Nitrogen
2560:carbon,
2517:Carboxyl
2484:Aldehyde
2472:Acryloyl
2454:carbonyl
2358:hydrogen
2313:Cumulene
2160:15285364
2031:26065934
1969:27936619
1819:(2007),
1777:22017381
1628:Archived
1502:: 47–51.
1328:94240406
1277:: 1–16.
1079:See also
1060:(TETA).
1001:linolein
955:glycidol
912:in base.
886:thiourea
681:carbonyl
579:and the
562:vanadium
558:titanium
506:epoxide
467:such as
199:ethylene
92:ethylene
76:volatile
72:nonpolar
68:reactive
3124:organic
2923:Selenol
2847:Sulfone
2800:Sulfide
2698:NONOate
2693:Nitroso
2683:Nitrite
2678:Nitrate
2668:Cyanate
2658:Nitrile
2643:Amidine
2638:Imidate
2608:Nitrene
2603:Hydrazo
2591:Enamine
2522:Acetoxy
2510:carboxy
2477:Benzoyl
2415:Epoxide
2398:Methoxy
2388:Alcohol
2342:Carbene
2276:Methine
1990:: 173.
1768:3288687
1625:Article
794:alcohol
727:toluene
675:In the
502:and/or
476:styrene
131:polymer
44:epoxide
3023:Iodide
2943:Selone
2787:Sulfur
2496:Ketone
2489:Ketene
2467:Acetyl
2422:Peroxy
2393:Alkoxy
2383:Acetal
2364:oxygen
2353:carbon
2337:Alkyne
2330:Benzyl
2325:Phenyl
2308:Allene
2303:Crotyl
2283:Alkene
2271:Bridge
2259:Pentyl
2244:Propyl
2234:Methyl
2168:847639
2166:
2158:
2060:: 29.
2029:
1967:
1926:
1829:
1798:
1775:
1765:
1663:
1421:
1326:
1206:
1171:
1122:
1067:Safety
879:alkene
790:reduce
707:, and
564:, and
426:enones
210:silver
203:oxygen
172:alkene
60:oxygen
56:carbon
3055:Other
2892:Boron
2862:Thial
2795:Thiol
2688:Nitro
2653:Imide
2633:Amide
2618:Oxime
2613:Imine
2586:Amine
2534:Ester
2501:Ynone
2405:Ether
2376:R-O-R
2351:Only
2293:Allyl
2288:Vinyl
2254:Butyl
2239:Ethyl
2229:Alkyl
2164:S2CID
2049:trans
1324:S2CID
1054:epoxy
788:both
776:epoxy
504:trans
478:with
177:Both
141:resin
136:epoxy
102:) is
48:ether
42:, an
2977:Halo
2462:Acyl
2362:and
2320:Aryl
2156:PMID
2027:PMID
1965:PMID
1924:ISBN
1827:ISBN
1796:ISBN
1773:PMID
1661:ISBN
1419:ISBN
1204:ISBN
1169:ISBN
1120:ISBN
917:Uses
870:and
609:.
594:The
528:for
472:CPBA
428:and
201:and
193:The
181:and
159:and
52:ring
2628:Azo
2148:doi
2120:doi
2093:doi
2062:doi
2019:doi
1992:doi
1957:doi
1953:116
1916:doi
1893:doi
1763:PMC
1755:doi
1751:112
1722:doi
1653:doi
1597:doi
1593:102
1565:doi
1538:doi
1449:doi
1378:doi
1374:117
1351:doi
1314:hdl
1306:doi
1279:doi
1252:doi
1227:doi
1196:doi
1161:doi
1112:doi
784:or
711:.)
530:C−C
523:O−O
500:cis
482:to
38:In
3143::
2360:,
2355:,
2162:.
2154:.
2144:23
2142:.
2116:58
2114:.
2089:94
2058:60
2025:.
2015:17
2013:.
1988:72
1986:.
1963:.
1951:.
1922:.
1889:32
1867:.
1771:.
1761:.
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1718:18
1716:.
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1691:;
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1534:95
1532:.
1500:11
1498:.
1477:;
1470:.
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1399:.
1372:.
1347:30
1345:.
1322:.
1312:.
1302:45
1300:.
1275:10
1273:.
1248:29
1246:.
1218:^
1202:.
1167:.
1118:.
881:.
844:OH
796:.
733:,
729:,
725:,
672:.
568:.
560:,
536:.
486::
452:)
380:Au
323:CO
247:CH
147:.
129:A
126:.
106:(C
94:(C
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2201:e
2194:t
2187:v
2170:.
2150::
2126:.
2122::
2099:.
2095::
2068:.
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2021::
1998:.
1994::
1971:.
1959::
1932:.
1918::
1899:.
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1567::
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1451::
1425:.
1403:.
1384:.
1380::
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1316::
1308::
1285:.
1281::
1258:.
1254::
1229::
1212:.
1198::
1177:.
1163::
1134:.
1114::
1011:.
905:.
873:n
842:n
840:)
838:4
836:H
834:2
830:4
828:H
826:2
772:N
635:.
470:m
355:O
347:2
343:H
338:2
335:+
327:2
318:2
315:+
312:O
304:4
300:H
291:2
287:C
282:6
271:2
267:O
262:6
259:+
251:2
242:=
238:C
230:2
226:H
221:7
112:4
110:H
108:2
100:4
98:H
96:2
20:)
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