248:
284:
97:
211:
186:
319:
which then attacks the second reaction partner. The arenium ion can also be formed by attack of the Lewis acid. The mechanisms are difficult to distinguish because many Lewis acids can behave as oxidants. Reactions taking place at room-temperature with well-known one-electron oxidizing agents likely
306:
is formed from one reaction partner by oxidation, in step two the radical ion attacks the second neutral partner in a substitution reaction and a new radical ion is formed with one ring bearing the positive charge and the other one the radical position. In step three dihydrogen is split off with
427:
Scholl, R. and Seer, C. (1912), Abspaltung aromatisch gebundenen
Wasserstoffs und Verknüpfung aromatischer Kerne durch Aluminiumchlorid. Justus Liebigs Ann. Chem., 394: 111–177.
379:
Scholl, R. and
Mansfeld, J. (1910), meso-Benzdianthron (Helianthron), meso-Naphthodianthron, und ein neuer Weg zum Flavanthren. Ber. Dtsch. Chem. Ges., 43: 1734–1746.
395:
Scholl, R., Seer, Chr. and
Weitzenböck, R. (1910), Perylen, ein hoch kondensierter aromatischer Kohlenwasserstoff C20H12. Ber. Dtsch. Chem. Ges., 43: 2202–2209.
123:
The protic acid in the Scholl reaction is often an impurity in the Lewis Acid and also formed in the course of a Scholl reaction. Reagents are
411:
Weitzenböck, R. and Seer, C. (1913), Zur
Kenntnis des Perylens und seiner Derivate. (2. Mitteilung). Ber. Dtsch. Chem. Ges., 46: 1994–2000.
56:
320:
proceed through a radical cation mechanism and reactions requiring elevated temperatures likely proceed through an arenium ion mechanism.
247:
508:
Christopher D. Simpson, Gunter
Mattersteig, Kai Martin, Lileta Gherghel, Roland E. Bauer, Hans Joachim Räder, and Klaus Müllen
451:
Benjamin T. King, Jií Kroulík, Charles R. Robertson, Pawel
Rempala, Cameron L. Hilton, Justin D. Korinek, and Lisa M. Gortari
269:
136:
344:
283:
555:
223:
292:
550:
49:
210:
535:
185:
560:
171:
144:
96:
8:
132:
261:
124:
509:
340:
175:
148:
140:
113:
74:
37:
517:
489:
460:
428:
412:
396:
380:
364:
273:
219:
506:
Nanosized
Molecular Propellers by Cyclodehydrogenation of Polyphenylene Dendrimers
116:. Perylene was also synthesised from 1,1’-binaphthalene in 1913. The synthesis of
237:
233:
128:
303:
167:
78:
416:
400:
544:
477:
452:
432:
384:
308:
90:
27:
162:
Given the high reaction temperature and the requirement for strongly acidic
368:
229:
156:
117:
316:
265:
109:
86:
493:
359:
Grzybowski, M., Skonieczny, K., Butenschön, H. and Gryko, D. T. (2013),
241:
201:
82:
521:
464:
179:
163:
105:
361:
Comparison of
Oxidative Aromatic Coupling and the Scholl Reaction
277:
232:
synthesis this reaction is advocated as an alternative for the
194:
174:
fare better than the intermolecular ones, for instance in the
104:
In 1910 Scholl reported the synthesis of a quinone and of
295:
is a research strategy in modern organic synthesis.
264:
is not known but could very well proceed through an
218:One study showed that the reaction lends itself to
240:of the product which can be prevented by blocking
170:often is low and the method is not a popular one.
542:
475:Vingiello, F. A.; Yanez, J.; Campbell, J. A.
298:Two mechanisms may compete. In step one of a
355:
353:
350:
315:one reaction partner is protonated to an
363:. Angew. Chem. Int. Ed., 52: 9900–9930.
543:
444:
442:
440:
255:
251:Scholl reaction Blocking Substituents
516:; 126(10) pp 3139 - 3147; (Article)
89:. It is named after its discoverer,
437:
270:electrophilic aromatic substitution
13:
459:; 72(7) pp 2279 - 2288; (Article)
337:March's Advanced Organic Chemistry
282:
246:
209:
184:
95:
14:
572:
214:An example of the Scholl reaction
189:An example of the Scholl reaction
228:In certain applications such as
224:polycyclic aromatic hydrocarbons
449:Controlling the Scholl Reaction
311:to the biaryl compound. In the
280:improve yield and selectivity:
499:
469:
421:
405:
389:
373:
329:
287:Scholl Reaction Para directors
1:
323:
293:oxidative coupling of phenols
143:etherate in dichloromethane,
7:
529:
10:
577:
536:Friedel-Crafts alkylation
417:10.1002/cber.191304602115
401:10.1002/cber.191004302175
236:. A recurring problem is
205:1-phenylbenz(a)anthracene
63:
43:
18:
433:10.1002/jlac.19123940202
385:10.1002/cber.19100430288
300:radical cation mechanism
193:Or the formation of the
172:Intramolecular reactions
556:Substitution reactions
369:10.1002/anie.201210238
288:
252:
215:
190:
145:Molybdenum(V) chloride
120:was reported in 1912.
101:
313:arenium ion mechanism
286:
250:
222:to form more complex
213:
188:
99:
335:M B Smith, J March.
198:dibenzo-(a.1)-pyrene
494:10.1021/jo00814a005
133:copper(II) chloride
100:The Scholl reaction
93:, a Swiss chemist.
551:Coupling reactions
289:
262:reaction mechanism
256:Reaction mechanism
253:
216:
191:
125:iron(III) chloride
102:
81:with the aid of a
522:10.1021/ja036732j
510:J. Am. Chem. Soc.
465:10.1021/jo061515x
274:Activating groups
220:cascade reactions
176:organic synthesis
149:lead tetraacetate
141:boron trifluoride
114:aluminum chloride
75:coupling reaction
67:
66:
38:Coupling reaction
568:
524:
503:
497:
473:
467:
446:
435:
425:
419:
409:
403:
393:
387:
377:
371:
357:
348:
333:
180:9-phenylfluorene
59:
19:Scholl reaction
16:
15:
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541:
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410:
406:
394:
390:
378:
374:
358:
351:
339:(Wiley, 2001) (
334:
330:
326:
309:rearomatisation
258:
238:oligomerization
234:Suzuki reaction
154:
129:dichloromethane
79:arene compounds
71:Scholl reaction
55:
12:
11:
5:
574:
564:
563:
561:Name reactions
558:
553:
539:
538:
531:
528:
526:
525:
498:
488:, 2053-2056. (
468:
436:
420:
404:
388:
372:
349:
327:
325:
322:
304:radical cation
257:
254:
244:substituents:
168:chemical yield
152:
65:
64:
61:
60:
53:
46:
45:
41:
40:
35:
34:Reaction type
31:
30:
25:
21:
20:
9:
6:
4:
3:
2:
573:
562:
559:
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554:
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523:
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511:
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491:
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483:
480:
479:
478:J. Org. Chem.
472:
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458:
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453:J. Org. Chem.
450:
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345:0-471-58589-0
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296:
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279:
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271:
268:. Just as in
267:
263:
249:
245:
243:
239:
235:
231:
226:
225:
221:
212:
208:
207:(66% yield).
206:
203:
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196:
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183:
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177:
173:
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146:
142:
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119:
115:
111:
107:
98:
94:
92:
91:Roland Scholl
88:
84:
80:
76:
72:
62:
58:
54:
51:
48:
47:
42:
39:
36:
33:
32:
29:
28:Roland Scholl
26:
23:
22:
17:
513:
505:
501:
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481:
476:
471:
456:
448:
423:
407:
391:
375:
360:
336:
331:
312:
299:
297:
290:
259:
230:triphenylene
227:
217:
204:
197:
192:
161:
157:acetonitrile
122:
118:Benzanthrone
103:
77:between two
70:
68:
57:RXNO:0000377
52:ontology ID
44:Identifiers
24:Named after
317:arenium ion
266:arenium ion
110:naphthalene
87:protic acid
545:Categories
324:References
260:The exact
242:tert-butyl
202:anthracene
112:both with
83:Lewis acid
200:from the
164:catalysts
530:See also
291:Indeed,
276:such as
106:perylene
278:methoxy
151:with BF
343:
195:pyrene
85:and a
108:from
73:is a
514:2004
482:1971
457:2007
341:ISBN
166:the
147:and
139:and
137:PIFA
69:The
518:doi
490:doi
461:doi
429:doi
413:doi
397:doi
381:doi
365:doi
178:of
155:in
127:in
50:RSC
547::
512:;
486:36
484:,
455:;
439:^
352:^
302:a
272:,
182::
159:.
135:,
131:,
520::
496:)
492::
463::
431::
415::
399::
383::
367::
347:)
153:3
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