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- Title
Addition of Benzenethiols to Silicon-Containing Enynes and Enynones.
- Authors
Sokov, S. A.; Gordon, K. V.; Zlotskii, S. S.; Golovanov, A. A.
- Abstract
Propynylidene derivatives of dimethyl malonate and Meldrumʼs acid, as well as cross-conjugated enynones, containing Me3Si, Et3Si, and t-BuMe2Si groups reacted with 4-methyl-, 4-methoxy-, and 4-chloro-benzenethiol under basic conditions to give the corresponding addition products with buta-1,3-diene and penta-1,4-dien-3-one fragments with high stereoselectivity. The thiylation products of enyne derivatives of dimethyl malonate and Meldrumʼs acid retain the trialkylsilyl group, whereas the addition of benzenethiols to 5-(tri-alkylsilyl)-1-phenylpent-1-en-4-yn-3-ones is accompanied by desilylation. Some mechanistic features of the described reactions have been established, and methods for the stereoselective synthesis of sulfur-containing polyunsaturated compounds have been developed.
- Subjects
ENYNES; POLYENES; ETHANES; CONJUGATE gradient methods
- Publication
Russian Journal of Organic Chemistry, 2024, Vol 60, Issue 1, p37
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428024010068