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
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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 | |||||||||
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| 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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| 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 |
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