SYNTHESIS OF 12-MEMBERED AND 13-MEMBERED SULFUR-CONTAINING LACTONES BY HOMOLYTIC MACROCYCLIZATION OF MERCAPTOACETIC ESTERS WITH ALKYNES

Authors
DEMCHUK DV LAZAREVA MI LINDEMAN SV KHRUSTALYOV VN STRUCHKOV YT ISMAGILOV RF TROYANSKY EI NIKISHIN GI
Citation
Dv. Demchuk et al., SYNTHESIS OF 12-MEMBERED AND 13-MEMBERED SULFUR-CONTAINING LACTONES BY HOMOLYTIC MACROCYCLIZATION OF MERCAPTOACETIC ESTERS WITH ALKYNES, Synthesis, (3), 1995, pp. 307-311
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1995
Pages
307 - 311
Database
ISI
SICI code
0039-7881(1995):3<307:SO1A1S>2.0.ZU;2-X
Abstract
Starting from mercaptoacetic acid esters of 1,2- or 1,3-diols and subs tituted 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 tripropylborane/oxygen system, includes generation of thiyl radicals and their addition to th e triple bond of alkynes.