Hydrochalcogenation of phenylthioacetylenes. Synthesis of mixed ( Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes

Hydrochalcogenation of phenylthioacetylenes. Synthesis of mixed ( Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes

The treatment of 1-phenylthioacetylenes with phenylselenolate and butyl or phenyltellurolate anions generated by the reaction of the corresponding dichalcogenide with NaBH 4 in aqueous ethanol results in the formation of mixed 1,2-bis(organylchalcogeno)-1-alkenes of Z configuration. The phenylthio g...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 42; no. 9; pp. 1595 - 1597
Main Authors: Dabdoub, Miguel J, Dabdoub, Vânia B, Pereira, Marco A
Format: Journal Article
Language:English
Published: Elsevier Ltd 26-02-2001
Online Access:Get full text
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Summary:The treatment of 1-phenylthioacetylenes with phenylselenolate and butyl or phenyltellurolate anions generated by the reaction of the corresponding dichalcogenide with NaBH 4 in aqueous ethanol results in the formation of mixed 1,2-bis(organylchalcogeno)-1-alkenes of Z configuration. The phenylthio group acts as a directing and activating group for the nucleophilic addition of the chalcogenate anions Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)02291-7