Rearrangement in the acetylenic nucleophilic substitution with the O-alkylcarbonodithioate anions

Authors
D'Yachkova, SG Beskrylaya, EA Gusarova, NK Trofimov, BA
Citation
Sg. D'Yachkova et al., Rearrangement in the acetylenic nucleophilic substitution with the O-alkylcarbonodithioate anions, PHOSPHOR SU, 158, 2000, pp. 81-89
Citations number
20
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
ISSN journal
10426507 → ACNP
Volume
158
Year of publication
2000
Pages
81 - 89
Database
ISI
SICI code
1042-6507(2000)158:<81:RITANS>2.0.ZU;2-0
Abstract
(Alkylthio)chloroacetylenes react with potassium O-alkyl carbonodithioates under mild conditions (25-30 degrees C, DMSO) to form an approximately equi molar mixture of O-alkyl-S-[2-(alkylthio)ethynyl] carbonodithioates and S-a lkyl-S-[2-(alkylthio)ethynyl] carbonodithioates in a total yield of up to 6 5%. The rearrangement is proved to occur in an anionic intermediate, probab ly, of the thiete structure.