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Synthesis 1995; 1995(3): 307-311
DOI: 10.1055/s-1995-3891
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Synthesis of 12- and 13-Membered Sulfur-Containing Lactones by Homolytic Macrocyclization of Mercaptoacetic Esters with Alkynes

Dmitry V. Demchuk* , Margarita I. Lazareva, Sergey V. Lindeman, Viktor N. Khrustalyov, Yurii T. Struchkov, Rustem F. Ismagilov, Emmanuil I. Troyansky, Gennady I. Nikishin
  • *N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 117913 Moscow, Russian Federation, Fax +7(095)1355328; E-mail L130@SUEARN2.FREE.MSK.SU
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Publication Date:
31 December 2000 (online)

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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.

thiacrown lactones - homolytic macrocyclization - tripropylborane