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Published March 1995 | Published
Journal Article Open

Synthesis of 12-Membered and 13-Membered Sulfur-Containing Lactones by Homolytic Macrocyclization of Mercaptoacetic Esters with Alkynes

Abstract

Starting from mercaptoacetic acid esters of 1,2- or 1,3-diols and substituted acetylenes 12- and 13-membered sulfur-containing lactones as 1:1 adducts were synthesized in yields up to 48%. The mechanism of this homolytic reaction, which is initiated by the tripropylborane/oxygen system, includes generation of thiyl radicals and their addition to the triple bond of alkynes.

Additional Information

© Georg Thieme Verlag, Rüdigerstr. Received 11 August 1994. The authors are grateful to the Russian Foundation of Fundamental Studies for financial support (Project 93-03-18110).

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August 22, 2023
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