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ALPHA-ALKYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDE DIMETHYLHYDRAZONES ACCOMPANIED WITH THE DOUBLE-BOND MIGRATION TO BETA,GAMMA

被引：9
作者：
YAMASHITA, M
MATSUMIYA, K
NAKANO, K
机构：
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 06期
关键词：
D O I：
10.1246/bcsj.66.1759
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Lithiated alpha,beta-unsaturated aldehyde N,N-dimethylhydrazones reacted with alkyl halides accompanied by double bond migration to give alpha-alkylated beta,gamma-unsaturated aldehyde N,N-dimethylhydrazones in satisfactory yields. This reaction was found to be caused at the first step by deprotonation from a gamma-carbon atom by lithium diisopropylamide. In the case of hydrazones with two kinds of gamma-protons, deprotonation from the less hindered gamma-carbon occurred selectively. Using this reaction, a novel sesquiterpene, 2,5,9-trimethyl-2-vinyl-4,8-decadienal. which has a vinyl group at the alpha-position, was synthesized in a good yield.
引用
收藏
页码：1759 / 1763
页数：5
相关论文
共 14 条
[1]  
Bergbreiter D.E., 1991, COMPREHENSIVE ORGANI, V2, P503
[2]   GENERATION AND SYNTHETIC USE OF METALLATED DIMETHYLHYDRAZONES REGION AND STEREOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS [J].
COREY, EJ ;
ENDERS, D .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04) :1337-1361
[3]  
HWA JCH, 1973, ORG SYNTH, V5, P608
[4]   REACTION OF 3-METHYL-2-CYCLOPENTEN-1-ONE N,N-DIMETHYLHYDRAZONE WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - A NOVEL SYNTHESIS OF BICYCLIC COMPOUNDS [J].
MATSUMIYA, K ;
GUO, YP ;
YAMASHITA, M .
CHEMISTRY LETTERS, 1992, (07) :1201-1202
[5]   ALPHA-ALKYLATION OF LITHIATED (2E, 4E)-2,4-ALKADIENAL DIMETHYLHYDRAZONES - PREPARATION OF ALPHA-ALKYLATED (3E, 5Z)-3,5-ALKADIENAL DIMETHYLHYDRAZONES [J].
MATSUMIYA, K ;
NAKANO, K ;
SUEMITSU, R ;
YAMASHITA, M .
CHEMISTRY LETTERS, 1988, (11) :1837-1838
[6]  
STOWELL JC, 1979, CARBANIONS ORGANIC S, P175
[7]  
TAKABE K, 1975, TETRAHEDRON LETT, P1237
[8]  
UJI Y, 1987, 31ST S CHEM TERP ESS
[9]   SIMPLE SYNTHESIS OF (Z)-12-NONADECEN-9-ONE, (Z)-13-ICOSEN-10-ONE, THE SEX-PHEROMONE OF PEACH FRUIT MOTH, AND (Z)-5-UNDECEN-2-ONE, A BIOLOGICALLY-ACTIVE MOLECULE FROM THE PEDAL GLAND OF THE BONTEBOK [J].
YAMASHITA, M ;
MATSUMIYA, K ;
MURAKAMI, K ;
SUEMITSU, R .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (09) :3368-3370
[10]   THE FACILE SYNTHESIS OF UNSYMMETRICAL KETONES USING ACETONE DIMETHYLHYDRAZONE [J].
YAMASHITA, M ;
MATSUMIYA, K ;
TANABE, M ;
SUEMITSU, R .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (01) :407-408
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