CaltechAUTHORS
  A Caltech Library Service

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

Demchuk, Dmitry V. and Lazareva, Margarita I. and Lindeman, Sergey V. and Khrustalyov, Viktor N. and Struchkov, Yurii T. and Ismagilov, Rustem F. and Troyansky, Emmanuil I. and Nikishin, Gennady I. (1995) Synthesis of 12-Membered and 13-Membered Sulfur-Containing Lactones by Homolytic Macrocyclization of Mercaptoacetic Esters with Alkynes. Synthesis-Stuttgart, 1995 (3). pp. 307-311. ISSN 0039-7881. doi:10.1055/s-1995-3891. https://resolver.caltech.edu/CaltechAUTHORS:20130821-160717675

[img] PDF - Published Version
See Usage Policy.

397kB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20130821-160717675

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1055/s-1995-3891DOIArticle
https://www.thieme-connect.com/ejournals/abstract/10.1055/s-1995-3891PublisherArticle
ORCID:
AuthorORCID
Ismagilov, Rustem F.0000-0002-3680-4399
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).
Funders:
Funding AgencyGrant Number
Russian Foundation for Fundamental Studies93-03-18110
Subject Keywords:thiacrown lactones; homolytic macrocyclization; tripropylborane crown-ethers; route
Issue or Number:3
DOI:10.1055/s-1995-3891
Record Number:CaltechAUTHORS:20130821-160717675
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130821-160717675
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:40787
Collection:CaltechAUTHORS
Deposited By: Whitney Barlow
Deposited On:23 Aug 2013 20:09
Last Modified:10 Nov 2021 00:08

Repository Staff Only: item control page