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

Authors

Dmitry V. Demchuk, Russian Academy of Sciences
Margarita I. Lazareva, Russian Academy of Sciences
Sergey Lindeman, Marquette UniversityFollow
Viktor N. Khrustalyov, Russian Academy of SciencesFollow
Yurii T. Struchkov, Russian Academy of SciencesFollow
Rustem F. Ismagilov, Russian Academy of Sciences
Emmanuil I. Troyansky, Russian Academy of Sciences
Gennady I. Nikishin, Russian Academy of SciencesFollow

Document Type

Article

Language

eng

Publication Date

1995

Publisher

Thieme

Source Publication

Synthesis

Source ISSN

0039-7881

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.

Comments

Synthesis, Vol. 1995, No. 3 (1995): 307-311. DOI.

Recommended Citation

Demchuk, Dmitry V.; Lazareva, Margarita I.; Lindeman, Sergey; Khrustalyov, Viktor N.; Struchkov, Yurii T.; Ismagilov, Rustem F.; Troyansky, Emmanuil I.; and Nikishin, Gennady I., "Synthesis of 12- and 13-Membered Sulfur-Containing Lactones by Homolytic Macrocyclization of Mercaptoacetic Esters with Alkynes" (1995). Chemistry Faculty Research and Publications. 813.
https://epublications.marquette.edu/chem_fac/813