SYNTHESIS OF AMINES VIA CARBON-SULFUR BOND CLEAVAGES OF SUBSTITUTED AMINOMETHYL SULFIDES WITH ORGANOLITHIUM REAGENTS - AMINOCARBENE ROUTE TO ENAMINES AND STERICALLY HINDERED AMINES

被引:13
作者
EISCH, JJ
MCNULTY, JF
SHI, X
机构
[1] Department of Chemistry, State University of New York, Binghamton
关键词
D O I
10.1021/jo00080a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Substituted and N,N-disubstituted aminomethyl sulfides can be converted into secondary and tertiary amines, respectively, by organolithium reagents in high yields, regardless of whether the N-substituent is alkyl or aryl; for the former case, imines, and for the latter case, aminocarbenes, are the most likely intermediates. © 1994, American Chemical Society. All rights reserved.
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页码:7 / 9
页数:3
相关论文
共 12 条
[1]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[2]   MONOALKYLATION OF PRIMARY AROMATIC-AMINES VIA N-(ALKOXYMETHYL)ARYL AMINES - EVIDENCE FOR THE FORMATION OF STABLE MONOMERIC METHYLENEAMINES [J].
BARLUENGA, J ;
BAYON, AM ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (19) :1109-1110
[3]   MONOALKYLATION OF PRIMARY ALIPHATIC-AMINES VIA "N-ALKYL-N-(ALKYLTHIOMETHYL)AMMONIUM CHLORIDES - EVIDENCE FOR THE FORMATION OF STABLE N-METHYLENEALKYLAMINES [J].
BARLUENGA, J ;
BAYON, AM ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) :427-428
[4]   IS N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE A GOOD LIGAND FOR LITHIUM [J].
COLLUM, DB .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (10) :448-454
[5]   SULFONE REAGENTS IN ORGANIC-SYNTHESIS .6. SULFONYL-SUBSTITUTED AND SILYL-SUBSTITUTED HYDROCARBONS AS VERSATILE CARBANION PRECURSORS IN ORGANIC-SYNTHESIS [J].
EISCH, JJ ;
BEHROOZ, M ;
DUA, SK .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :121-136
[6]   SULFONE REAGENTS IN ORGANIC-SYNTHESIS .7. [(PHENYLSULFONYL)METHYLENE]DILITHIUM AS A NOVEL CYCLIZING AND HOMOLOGIZING REAGENT FOR BIFUNCTIONAL ORGANIC SUBSTRATES [J].
EISCH, JJ ;
DUA, SK ;
BEHROOZ, M .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3674-3676
[7]   FUNCTIONALIZED ORGANOLITHIUM REAGENTS .9. LITHIATION AND ISOMERIZATION OF ALLYLIC AMINES AS A GENERAL-ROUTE TO ENAMINES AND THEIR CARBONYL DERIVATIVES [J].
EISCH, JJ ;
SHAH, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2955-2957
[8]   CONDENSATION OF THIOPHENOLS AND FORMALDEHYDE WITH SOME AROMATIC AMINES [J].
GRILLOT, GF ;
SCHAFFRATH, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (08) :1035-1038
[9]   REACTION OF GRIGNARD REAGENTS WITH ARYLTHIOMETHYLARYLAMINES AND WITH TRTS(PHENYLTHIOMETHYL)AMINES [J].
POLLAK, IE ;
GRILLOT, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (09) :2892-&
[10]   REACTION OF GRIGNARD REAGENTS WITH N,N-DIALKYL-N-(PHENYLTHIOMETHYL)AMINES [J].
POLLAK, IE ;
TRIFUNAC, AD ;
GRILLOT, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :272-&