BEHAVIOR OF ARYLAZO TERT-BUTYL SULFIDES WITH KETONE ENOLATES - COMPETITION BETWEEN SRN1 ALPHA-ARYLATION AND AZOCOUPLING REACTIONS

被引:34
作者
DELLERBA, C [1 ]
NOVI, M [1 ]
PETRILLO, G [1 ]
TAVANI, C [1 ]
机构
[1] CNR,CTR STUDIO DIARILOIDI & LORO APPLICAZ,IST CHIM ORGAN,CORSO EUROPA 26,I-16132 GENOA,ITALY
关键词
D O I
10.1016/S0040-4020(01)88144-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Z)-Arylazo tert-butyl sulfides 1a-i react, in DMSO and at room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous S(RN)1 dark reactions. Alpha-Phenylation of pinacolone and acetophenone enolates by 1a likewise occurs in excellent yields. In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution product 13. With azosulfides 1j-m the arylation pathway competes with a base-induced thiol elimination eventually leading, depending on the structure of the azosulfide, to indazoles 8 or 11 and/or to 2-oxopropanal arylhydrazones 9, 10 or 12.
引用
收藏
页码:325 / 334
页数:10
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