Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones

被引：20

作者：

Golovanov, A. A. ^{[1
]}

Gusev, D. M. ^{[1
]}

Vologzhanina, A. V. ^{[2
]}

Bekin, V. V. ^{[1
]}

Pisareva, V. S. ^{[1
]}

机构：

[1] Togliatti State Univ, Tolyatti 445667, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 50卷 / 01期

关键词：

MICHAEL ADDITION; THIOLS; KETONES;

D O I：

10.1134/S1070428014010035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselectivity of nucleophilic addition of benzenethiols and phenylmethanethiol to 1,5-diarylpent-2-en-4-yn-1-ones in ethanol in the presence of triethylamine at 0-30A degrees C is determined by the nucleophile nature. Phenylmethanethiol adds to the double bond, whereas benzenethiols add to the triple bond. The addition products, 1,5-diaryl-3-benzylsulfanylpent-4-yn-1-ones and 1,5-diaryl-5-(4-arylsulfanyl)penta-2,4-dien-1-ones, respectively, were isolated in 43-89% yield. Substituents in the aryl rings of the substrates did not affect the reaction direction.

引用

页码：13 / 20

页数：8

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