591:
584:
532:
577:
237:
162:
546:
539:
570:
553:
27:
681:
427:
511:
methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form. This conformation was confirmed by
Allinger and co-workers. The
795:
Dorofeeva, O. V.; Mastryukov, V. S.; Allinger, N. L.; Almenningen, A. (1985). "The molecular structure and conformation of cyclooctane as determined by electron diffraction and molecular mechanics calculations".
675:. Work in 2009 on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.
944:
Thomas
Schiffer, Georg Oenbrink, “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.
440:
822:
286:
962:
Deng, Guojun; Wenwen Chen; Chao-Jun Li (February 2009). "An
Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes".
768:
512:
crown conformation (below) is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S
1007:
715:
435:
251:
447:
766:
Hendrickson, James B. (1967). "Molecular
Geometry V. Evaluation of Functions and Conformations of Medium Rings".
498:
861:
Pakes, P. W.; Rounds, T. C.; Strauss, H. L. (1981). "Conformations of cyclooctane and some related oxocanes".
1113:
1108:
194:
157:
215:
119:
1000:
625:
672:
232:
508:
384:
794:
667:
Cyclooctane participates in no reactions except those typical of other saturated hydrocarbons,
482:, but it is often a reference compound for saturated eight-membered ring compounds in general.
1103:
993:
633:
632:(COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for
590:
504:
99:
583:
203:
39:
139:
8:
75:
65:
927:
629:
236:
161:
531:
919:
878:
748:
711:
707:
Handbook of
Physical-chemical Properties and Environmental Fate for Organic Chemicals
576:
467:
931:
832:
1082:
971:
945:
909:
870:
836:
827:
805:
777:
740:
372:
309:
538:
705:
545:
183:
897:
1077:
569:
418:
1097:
1072:
1067:
949:
923:
882:
831:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
552:
361:
351:
150:
914:
840:
1047:
1037:
1027:
975:
752:
744:
409:
1062:
1057:
1042:
1032:
1016:
479:
463:
403:
874:
809:
781:
680:
668:
620:
The main route to cyclooctane derivatives involves the dimerization of
331:
130:
621:
417:
Except where otherwise noted, data are given for materials in their
898:"Basic terminology of stereochemistry (IUPAC Recommendations 1996)"
98:
26:
486:
341:
170:
985:
517:
110:
640:, produces cyclooctane, which is usually discarded or burnt:
88:
220:
961:
731:
860:
507:of cyclooctane has been studied extensively using
1095:
182:
74:
759:
628:. This process affords, among other products,
1001:
356:14.59 °C (58.26 °F; 287.74 K)
788:
499:Macrocyclic stereocontrol § Cyclooctane
765:
730:
636:. The activation of these catalysts under H
624:, catalysed by nickel(0) complexes such as
1008:
994:
816:
615:
235:
160:
138:
913:
202:
769:Journal of the American Chemical Society
684:Amination of cyclooctane by nitrobenzene
679:
260:InChI=1S/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2
270:InChI=1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2
231:
1096:
703:
366:149 °C (300 °F; 422 K)
151:
989:
938:
697:
263:Key: WJTCGQSWYFHTAC-UHFFFAOYSA-N
118:
895:
856:
854:
852:
850:
848:
955:
273:Key: WJTCGQSWYFHTAC-UHFFFAOYAO
173:
13:
964:Advanced Synthesis & Catalysis
828:Compendium of Chemical Terminology
14:
1125:
863:The Journal of Physical Chemistry
845:
798:The Journal of Physical Chemistry
1015:
589:
582:
575:
568:
551:
544:
537:
530:
492:
425:
321:
25:
421:(at 25 °C , 100 kPa).
889:
724:
315:
1:
690:
478:. It is a simple colourless
7:
10:
1130:
902:Pure and Applied Chemistry
710:. CRC Press. p. 258.
626:nickel bis(cyclooctadiene)
496:
336:112.21 g/mol
1023:
673:free radical halogenation
562:
559:
415:
395:
302:
282:
247:
58:
50:
38:
33:
24:
950:10.1002/14356007.a08_205
915:10.1351/pac199668122193
841:10.1351/goldbook.C01422
704:Mackay, Donald (2006).
616:Synthesis and reactions
385:Magnetic susceptibility
976:10.1002/adsc.200800689
745:10.1002/anie.200600782
685:
683:
634:homogeneous catalysis
497:Further information:
1114:Eight-membered rings
1109:Hydrocarbon solvents
896:Moss, G. P. (1996).
733:Angew. Chem. Int. Ed
40:Preferred IUPAC name
875:10.1021/j150617a013
810:10.1021/j100248a015
782:10.1021/ja01002a036
526:
373:Solubility in water
21:
833:crown conformation
686:
630:1,5-cyclooctadiene
607:Twist chair-chair
525:
485:Cyclooctane has a
448:Infobox references
396:Related compounds
19:
1091:
1090:
908:(12): 2193–2222.
869:(17): 2469–2475.
776:(26): 7036–7043.
739:(38): 6254–6261.
717:978-1-56670-687-2
611:
610:
604:Twist boat-chair
468:molecular formula
456:Chemical compound
454:
453:
216:CompTox Dashboard
100:Interactive image
16:Chemical compound
1121:
1083:Cyclotetradecane
1010:
1003:
996:
987:
986:
980:
979:
959:
953:
942:
936:
935:
917:
893:
887:
886:
858:
843:
820:
814:
813:
792:
786:
785:
763:
757:
756:
728:
722:
721:
701:
593:
586:
579:
572:
555:
548:
541:
534:
527:
524:
438:
432:
429:
428:
391:−91.4·10 cm/mol
323:
317:
310:Chemical formula
240:
239:
224:
222:
206:
186:
175:
164:
153:
142:
122:
102:
78:
29:
22:
18:
1129:
1128:
1124:
1123:
1122:
1120:
1119:
1118:
1094:
1093:
1092:
1087:
1019:
1014:
984:
983:
960:
956:
943:
939:
894:
890:
859:
846:
821:
817:
793:
789:
764:
760:
729:
725:
718:
702:
698:
693:
663:
659:
655:
651:
647:
639:
618:
515:
501:
495:
477:
473:
457:
450:
445:
444:
443: ?)
434:
430:
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422:
406:
388:
375:
326:
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312:
298:
295:
290:
289:
278:
275:
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255:
254:
243:
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209:
189:
176:
145:
125:
105:
92:
81:
68:
54:
46:
45:
17:
12:
11:
5:
1127:
1117:
1116:
1111:
1106:
1089:
1088:
1086:
1085:
1080:
1078:Cyclotridecane
1075:
1070:
1065:
1060:
1055:
1050:
1045:
1040:
1035:
1030:
1024:
1021:
1020:
1013:
1012:
1005:
998:
990:
982:
981:
970:(3): 353–356.
954:
937:
888:
844:
815:
804:(2): 252–257.
787:
758:
723:
716:
695:
694:
692:
689:
688:
687:
665:
664:
661:
657:
653:
649:
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637:
617:
614:
613:
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609:
608:
605:
602:
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587:
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573:
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564:
561:
557:
556:
549:
542:
535:
513:
494:
491:
475:
471:
455:
452:
451:
446:
424:
423:
419:standard state
416:
413:
412:
407:
401:
398:
397:
393:
392:
389:
383:
380:
379:
376:
371:
368:
367:
364:
358:
357:
354:
348:
347:
344:
338:
337:
334:
328:
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324:
318:
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285:
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169:
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135:
133:
127:
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124:
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115:
113:
107:
106:
104:
103:
95:
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71:
69:
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61:
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56:
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43:
42:
36:
35:
31:
30:
15:
9:
6:
4:
3:
2:
1126:
1115:
1112:
1110:
1107:
1105:
1102:
1101:
1099:
1084:
1081:
1079:
1076:
1074:
1073:Cyclododecane
1071:
1069:
1068:Cycloundecane
1066:
1064:
1061:
1059:
1056:
1054:
1051:
1049:
1046:
1044:
1041:
1039:
1036:
1034:
1031:
1029:
1026:
1025:
1022:
1018:
1011:
1006:
1004:
999:
997:
992:
991:
988:
977:
973:
969:
965:
958:
951:
947:
941:
933:
929:
925:
921:
916:
911:
907:
903:
899:
892:
884:
880:
876:
872:
868:
864:
857:
855:
853:
851:
849:
842:
838:
834:
830:
829:
824:
819:
811:
807:
803:
799:
791:
783:
779:
775:
771:
770:
762:
754:
750:
746:
742:
738:
734:
727:
719:
713:
709:
708:
700:
696:
682:
678:
677:
676:
674:
670:
643:
642:
641:
635:
631:
627:
623:
606:
603:
600:
597:
596:
592:
588:
585:
581:
578:
574:
571:
567:
566:
558:
554:
550:
547:
543:
540:
536:
533:
529:
528:
523:
522:
521:
519:
510:
509:computational
506:
500:
493:Conformations
490:
488:
487:camphoraceous
483:
481:
469:
465:
461:
449:
442:
437:
420:
414:
411:
408:
405:
400:
399:
394:
390:
386:
382:
381:
377:
374:
370:
369:
365:
363:
362:Boiling point
360:
359:
355:
353:
352:Melting point
350:
349:
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343:
340:
339:
335:
333:
330:
329:
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306:
301:
292:
291:
288:
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267:
257:
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246:
238:
234:
233:DTXSID9075377
230:
229:
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217:
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205:
201:
200:
198:
196:
193:
192:
185:
181:
180:
178:
172:
168:
167:
163:
159:
156:
154:
152:ECHA InfoCard
149:
148:
141:
137:
136:
134:
132:
129:
128:
121:
117:
116:
114:
112:
109:
108:
101:
97:
96:
94:
90:
85:
84:
77:
73:
72:
70:
67:
63:
62:
57:
49:
41:
37:
32:
28:
23:
1104:Cycloalkanes
1052:
1048:Cycloheptane
1038:Cyclopentane
1028:Cyclopropane
1017:Cycloalkanes
967:
963:
957:
940:
905:
901:
891:
866:
862:
826:
818:
801:
797:
790:
773:
767:
761:
736:
732:
726:
706:
699:
666:
619:
516:, elemental
505:conformation
502:
484:
459:
458:
410:Cycloheptane
404:cycloalkanes
120:ChEMBL452651
59:Identifiers
53:Cyclo-octane
51:Other names
20:Cyclooctane
1063:Cyclodecane
1058:Cyclononane
1053:Cyclooctane
1043:Cyclohexane
1033:Cyclobutane
560:Boat-chair
480:hydrocarbon
464:cycloalkane
460:Cyclooctane
346:0.834 g/cm
303:Properties
158:100.005.484
44:Cyclooctane
1098:Categories
691:References
669:combustion
601:Boat-boat
378:7.90 mg/L
332:Molar mass
294:C1CCCCCCC1
204:KKZ3KBS654
131:ChemSpider
87:3D model (
66:CAS Number
924:0033-4545
883:0022-3654
622:butadiene
466:with the
932:98272391
753:16983730
402:Related
387:(χ)
76:292-64-8
441:what is
439: (
342:Density
171:PubChem
930:
922:
881:
751:
714:
652:+ 2 H
563:Crown
518:sulfur
489:odor.
436:verify
433:
287:SMILES
111:ChEMBL
34:Names
928:S2CID
823:IUPAC
656:→ C
462:is a
252:InChI
89:JSmol
920:ISSN
879:ISSN
749:PMID
712:ISBN
671:and
598:Tub
503:The
195:UNII
184:9266
140:8909
972:doi
968:351
946:doi
910:doi
871:doi
837:doi
835:".
806:doi
778:doi
741:doi
470:(CH
221:EPA
174:CID
1100::
966:.
926:.
918:.
906:68
904:.
900:.
877:.
867:85
865:.
847:^
825:,
802:89
800:.
774:89
772:.
747:.
737:45
735:.
662:16
650:12
520:.
325:16
1009:e
1002:t
995:v
978:.
974::
952:.
948::
934:.
912::
885:.
873::
839::
812:.
808::
784:.
780::
755:.
743::
720:.
660:H
658:8
654:2
648:H
646:8
644:C
638:2
514:8
476:8
474:)
472:2
431:Y
322:H
319:8
316:C
223:)
219:(
91:)
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