NEW SYNTHETIC REACTIONS BASED ON THE ONIUM SALTS OF AZA-ARENES

被引:320
作者
MUKAIYAMA, T
机构
[1] Department of Chemistry, Faculty of Science, The University of Tokyo, Tokyo, 113, Hongo
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 10期
关键词
Aza‐arenes; Onium compounds; Synthetic methods;
D O I
10.1002/anie.197907073
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Effective syntheses employing 2‐halogenated pyridinium, benzoxazolium, benzothiazolium, and pyridinium salts have been accomplished in the absence of strong acids and bases. Activation of carboxylic acids or alcohols with these onium salts leads to 2‐acyloxy and 2‐alkoxy intermediates which can be transformed into esters, amides, thiol esters, (macrocyclic) lactones, acid fluorides, olefins, allenes, carbodiimides isocyanates, isothiocyanates, nitriles, and isocyanates. The possibility of performing stereospecific syntheses (involving configurational inversion) with onium salts deserves attention. Copyright © 1979 by Verlag Chemie, GmbH, Germany
引用
收藏
页码:707 / 721
页数:15
相关论文
共 108 条
[1]   ULTRAVIOLET SPECTRA AND STRUCTURES OF THE PYRIDO [1,2-A]PYRIMIDONES [J].
ADAMS, R ;
PACHTER, IJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (21) :5491-5497
[2]   GRIGNARD SYNTHESIS OF 2-PHENYL-2-BUTANOL IN OPTICALLY ACTIVE SOLVENTS [J].
ALLENTOFF, N ;
WRIGHT, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (01) :1-6
[3]   ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH CHIRAL HYDRIDE REAGENTS PREPARED FROM LITHIUM ALUMINUM-HYDRIDE AND (S)-2-(N-SUBSTITUTED AMINOMETHYL)PYRROLIDINES [J].
ASAMI, M ;
OHNO, H ;
KOBAYASHI, S ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (06) :1869-1873
[4]   FACILE SYNTHESIS OF CARBOXAMIDES BY USING 1-METHYL-2-HALOPYRIDINIUM IODIDES AS COUPLING REAGENTS [J].
BALD, E ;
SAIGO, K ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1975, (11) :1163-1166
[5]  
BALD E, 1976, HETEROCYCLES, P1707
[6]  
BERETTA E, 1974, SYNTHESIS-STUTTGART, P425
[7]  
BRAUER HJ, 1972, TETRAHEDRON LETT, P5227
[8]   THE BECKMANN REARRANGEMENT OF THE OXIMES OF ALKYL PHENYL KETONES [J].
BROWN, RF ;
VANGULICK, NM ;
SCHMID, GH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (05) :1094-1097
[9]   A 1-STEP CONVERSIONOF CYCLOHEXENE OXIDE INTO CIS-1,2-DICHLOROCYCLOHEXANE [J].
CAMPBELL, JR ;
JONES, JKN ;
WOLFE, S .
CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (19) :2339-&
[10]  
COREY EJ, 1976, TETRAHEDRON LETT, P3409