Synthesis of α-phenylselanyl and α-phenylsulfanyl nitriles from aldehyde N,N-dialkylhydrazones

被引：3

作者：

Ternon, M ^{[1
]}

Pannecoucke, X ^{[1
]}

Outurquin, F ^{[1
]}

Paulmier, C ^{[1
]}

机构：

[1] Univ Rouen, Lab Synth Thio & Seleno Organ, IRCOF UFR Sci, F-76821 Mont St Aignan, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 16期

关键词：

hydrazone; SAMP; deprotonation; nitrile;

D O I：

10.1016/S0040-4020(02)00232-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phenylselenenylation of azaenolates, formed by LDA treatment of dimethylhydrazones 1 (R-2=H) and derived from linear aliphatic aldehydes, has led to alpha-phenylselanyl hydrazones 2. alpha-Phenylselanyl nitriles 3 were, however, isolated when an excess of base and of PhSeX (X=Cl, Br) were used. Hydrazones 1 bearing an alpha-alkyl substituent (R(2)not equalH) gave also nitriles 3. SAMP-hydrazones 4 showed the same reactivity and the corresponding nitriles 3 were obtained in a racemic form. The use of PhSCl, in the place of PhSeBr, has led to alpha-phenylsulfanyl nitriles 6 from hydrazones I derived from alpha-branched aldehydes (R(2)not equalH). (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3275 / 3279

页数：5

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