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

…, MI Lazareva, SV Lindeman, VN Khrustalyov…

Index: Demchuk; Lazareva; Lindeman; Khrustalyov; Struchkov; Ismagilov; Troyansky; Nikishin Synthesis, 1995 , # 3 p. 307 - 311

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Citation Number: 13

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 synthesised in yields up to 48%. The mechanism of this homolytic reaction, which is initiated by the tripropylb0rane/ oxygen system, includes generation of thiyl radicals and their addition to the triple bond of alkynes. Condensation of dihalides or ditosylates with glycols or dithiols presents the most ...