Thiophenols Addition Reactions to Siliconcontaining Enynes and Enynones

S. A. Sokov; Соков С. А.; K. V. Gordon; Гордон К. В.; S. S. Zlotskii; Злотский С. С.; A. A. Golovanov; Голованов А. А.

doi:10.31857/S0514749224010106

Thiophenols Addition Reactions to Siliconcontaining Enynes and Enynones

Authors: Sokov S.A.¹^,2, Gordon K.V.¹, Zlotskii S.S.², Golovanov A.A.¹
Affiliations:
1. Togliatti State University
2. Ufa State Petroleum Technological University
Issue: Vol 60, No 1 (2024)
Pages: 109-119
Section: Articles
URL: https://freezetech.ru/0514-7492/article/view/672249
DOI: https://doi.org/10.31857/S0514749224010106
EDN: https://elibrary.ru/EMTMGC
ID: 672249

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Abstract

As well as the cross-conjugated enynones, propynylidene derivatives of malonic ester and Meldrum’s acid that contain Me₃Si, Et₃Si and t-BuMe₂Si groups, attach stereoselectively 4-methyl-, 4-methoxy- and 4-chlorothiophenol under conditions of base catalysis. In the process, there are sulfanilic compounds containing buta-1,3-diene and penta-1,4-dien-3-one fragments formed in high yields. In the thiylation products of the enyne derivatives of malonic ester and Meldrum’s acid, Me₃Si, Et₃Si and t-BuMe₂Si groups are retained; desilylation occurs during the thiylation of 5-trialkylsilyl-1-phenylpent-1-en-4-yn-3-ones. There are some certain regularities determined for observed reactions. We also developed stereoselective methods for the S-containing polyunsaturated compounds obtaining.

Keywords

Meldrum’s acid, malonic ester, nucleophilic addition, thiophenols, reactivity, stereoselectivity, dienes, enynes, C-nucleophiles reactivity, trialkylsilyl protecting groups

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