GENERATION AND REACTIONS OF N-(ALPHA-LITHIOALKYL)TETRAZOLES

被引:21
作者
MOODY, CJ
REES, CW
YOUNG, RG
机构
[1] Department of Chemistry, Imperial College of Science, Technology and Medicine
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 02期
关键词
D O I
10.1039/p19910000323
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 1-alkyl-4 and 2-alkyl-5-phenyltetrazoles 10 with t-butyllithium in tetrahydrofuran at -78-degrees-C gives 'dipole-stabilised' alpha-lithioalkyl derivatives 2 and 3 which are readily converted into the corresponding deuteriated, silylated, alkylated, hydroxymethylated, acylated and carboxylated derivatives 5 and 11, mostly in high yield (Tables 1 and 2). Lithiation of 5-phenyl-2-trimethylsilylmethyltetrazole 10c, prepared in this way, followed by reaction with aldehydes results in Peterson olefination to give 2-alkenyltetrazoles 11g, h in good yield.
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页码:323 / 327
页数:5
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