236:
139:
experiments with two different carboxylic acids. With two different carboxylic acids, the reaction behaves poorly because of poor selectivity except when one of the acids (for example, a small, volatile one) is used in large excess.
123:
via decarboxylation of one of the acid groups prior to the nucleophilic attack has been proposed, but is unlikely since the byproduct resulting from the carbanion's
246:
illustrates the production of the metal carboxylate in situ. Iron powder and butyric acid are converted to iron butyrate. Pyrolysis of that salt gives the ketone.
264:
374:
516:
366:
128:
215:
360:
55:
172:
132:
100:
208:
116:
96:
411:
370:
188:
136:
492:
465:
438:
403:
341:
310:
279:
227:
184:
92:
27:
235:
157:
149:
35:
31:
223:
168:
63:
391:
510:
392:"Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass"
204:
176:
104:
243:
219:
180:
161:
124:
200:
496:
469:
442:
314:
120:
415:
407:
283:
483:
Davis, Robert; Granito, Charles; Schultz, Harry P. (1967). "4-Heptanone".
359:
Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996).
265:"Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope"
203:, which is potentially of interest as a diesel fuel, can be produced from
196:
108:
345:
54:) by the application of heat. It can be thought of as a decarboxylative
192:
153:
135:
mechanism and is characterised by a different product distribution in
127:
by the acid has never been reported. This reaction is different from
43:
329:
298:
164:
ketonization was the premier commercial method for its production.
119:
with the decarboxylation. The initial formation of an intermediate
59:
16:
Chemical reaction which converts two –COOH groups to >C=O
390:
Pileidis, Filoklis D.; Titirici, Maria-Magdalena (2016).
183:. Of commercial interest are related ketonizations using
456:
Thorpe, J. F.; Kon, G. A. R. (1925). "Cyclopentanone".
362:
Vogel's
Textbook of Practical Organic Chemistry 5th Ed
365:. London: Longman Science & Technical. p.
429:A. G. Dobson and H. H. Hatt (1953). "Stearone".
330:"Improvement in the Manufacture of Acetone.1"
8:
107:of one acid group on the other acid group's
234:
334:Journal of the American Chemical Society
84:
80:
76:
72:
49:
255:
7:
218:ketonization is the conversion of
207:. Stearone is prepared by heating
14:
303:Annalen der Chemie und Pharmacie
34:converting two equivalents of a
299:"Ueber s. G. gemischte Acetone"
1:
58:of two identical molecules.
24:decarboxylative ketonization
167:Ketonic decarboxylation of
131:, which proceeds through a
95:promote this reaction. The
533:
286:– via The Vespiary.
129:oxidative decarboxylation
497:10.15227/orgsyn.047.0075
470:10.15227/orgsyn.005.0037
443:10.15227/orgsyn.033.0084
315:10.1002/jlac.18581080124
148:The dry distillation of
20:Ketonic decarboxylation
408:10.1002/cssc.201501405
328:Squibb, E. R. (1895).
284:10.1002/ejoc.200400546
297:Friedel, C. (1858).
56:Claisen condensation
346:10.1021/ja02158a004
173:manganese(II) oxide
101:nucleophilic attack
209:magnesium stearate
160:in 1858 and until
117:concerted reaction
97:reaction mechanism
517:Organic reactions
485:Organic Syntheses
431:Organic Syntheses
272:Eur. J. Org. Chem
242:The synthesis of
189:manganese dioxide
137:isotopic labeling
115:), possibly as a
42:) to a symmetric
524:
501:
500:
480:
474:
473:
453:
447:
446:
426:
420:
419:
387:
381:
380:
356:
350:
349:
325:
319:
318:
294:
288:
287:
269:
263:Renz, M (2005).
260:
238:
228:barium hydroxide
185:cerium(IV) oxide
156:was reported by
114:
99:likely involves
88:
66:are byproducts:
53:
41:
28:organic reaction
532:
531:
527:
526:
525:
523:
522:
521:
507:
506:
505:
504:
482:
481:
477:
455:
454:
450:
428:
427:
423:
389:
388:
384:
377:
358:
357:
353:
327:
326:
322:
296:
295:
291:
267:
262:
261:
257:
252:
158:Charles Friedel
150:calcium acetate
146:
112:
86:
82:
78:
74:
70:
51:
47:
39:
36:carboxylic acid
32:decarboxylation
26:) is a type of
22:(also known as
17:
12:
11:
5:
530:
528:
520:
519:
509:
508:
503:
502:
475:
448:
421:
402:(6): 562–582.
382:
375:
351:
340:(3): 187–201.
320:
289:
278:(6): 979–988.
254:
253:
251:
248:
240:
239:
224:cyclopentanone
216:intramolecular
214:An example of
175:catalyst in a
169:propanoic acid
145:
142:
90:
89:
64:carbon dioxide
15:
13:
10:
9:
6:
4:
3:
2:
529:
518:
515:
514:
512:
498:
494:
490:
486:
479:
476:
471:
467:
463:
459:
452:
449:
444:
440:
436:
432:
425:
422:
417:
413:
409:
405:
401:
397:
393:
386:
383:
378:
376:9780582462366
372:
368:
364:
363:
355:
352:
347:
343:
339:
335:
331:
324:
321:
316:
312:
308:
304:
300:
293:
290:
285:
281:
277:
273:
266:
259:
256:
249:
247:
245:
237:
233:
232:
231:
229:
225:
221:
217:
212:
210:
206:
202:
198:
194:
190:
186:
182:
178:
174:
170:
165:
163:
159:
155:
151:
143:
141:
138:
134:
130:
126:
122:
118:
110:
106:
102:
98:
94:
69:
68:
67:
65:
61:
57:
45:
37:
33:
29:
25:
21:
488:
484:
478:
461:
457:
451:
434:
430:
424:
399:
395:
385:
361:
354:
337:
333:
323:
306:
302:
292:
275:
271:
258:
241:
213:
205:valeric acid
177:tube furnace
166:
147:
105:alpha-carbon
91:
23:
19:
18:
396:ChemSusChem
309:: 122–125.
244:4-heptanone
220:adipic acid
181:3-pentanone
162:World War I
125:protonation
458:Org. Synth
250:References
201:5-Nonanone
197:catalysts
121:carbanion
40:R−C(=O)OH
511:Category
416:26847212
179:affords
152:to give
144:Examples
109:carbonyl
195:as the
193:alumina
171:over a
154:acetone
133:radical
103:of the
79:CO + CO
75:H → R
491:: 75.
464:: 37.
437:: 84.
414:
373:
44:ketone
30:and a
268:(PDF)
226:with
93:Bases
71:2 RCO
60:Water
412:PMID
371:ISBN
276:2005
187:and
62:and
493:doi
466:doi
439:doi
404:doi
367:613
342:doi
311:doi
307:108
280:doi
222:to
191:on
113:C=O
83:+ H
52:C=O
513::
489:47
487:.
460:.
435:33
433:.
410:.
398:.
394:.
369:.
338:17
336:.
332:.
305:.
301:.
274:.
270:.
230:.
211:.
199:.
499:.
495::
472:.
468::
462:5
445:.
441::
418:.
406::
400:9
379:.
348:.
344::
317:.
313::
282::
111:(
87:O
85:2
81:2
77:2
73:2
50:2
48:R
46:(
38:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.