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

Authors
Dabdoub, MJ Dabdoub, VB Pereira, MA
Citation
Mj. Dabdoub et al., Hydrochalcogenation of phenylthioacetylenes. Synthesis of mixed (Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes, TETRAHEDR L, 42(9), 2001, pp. 1595-1597
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1595 - 1597
Database
ISI
SICI code
0040-4039(20010226)42:9<1595:HOPSOM>2.0.ZU;2-1
Abstract
The treatment of 1-phenylthioacetylenes with phenylselenolate and butyl or phenyltellurolate anions generated by the reaction of the corresponding dic halcogenide with NaBH4 in aqueous ethanol results in the formation of mixed 1,2-bis(organylchalcogeno)-1-alkenes of Z configuration. The phenylthio gr oup acts as a directing and activating group for the nucleophilic addition of the chalcogenate anions (C) 2001 Elsevier Science Ltd. All rights reserv ed.