Synthesis of ketene (S, Te)acetals and their transformation into Z-alpha-phenylthio-alpha,beta-unsaturated aldehydes

Authors
Silveira, CC Perin, G Braga, AL Dabdoub, MJ Jacob, RG
Citation
Cc. Silveira et al., Synthesis of ketene (S, Te)acetals and their transformation into Z-alpha-phenylthio-alpha,beta-unsaturated aldehydes, TETRAHEDRON, 55(24), 1999, pp. 7421-7432
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
24
Year of publication
1999
Pages
7421 - 7432
Database
ISI
SICI code
0040-4020(19990611)55:24<7421:SOK(TA>2.0.ZU;2-9
Abstract
Reaction of thiomethyl phosphonates with aryl (or butyl) tellurenyl halides and aldehydes under basic conditions provides moderate to good yields of k etene thio (telluro) acetals, with vinylic sulfides being byproducts of thi s transformation. Tellurium-lithium exchange by reaction with n-BuLi yielde d vinyl organolithium species, which were captured with several electrophil es. In the case of DMF, Z,alpha-phenylthio-alpha,beta-unsaturaled aldehydes were obtained. (C) 1999 EIsevier Science Ltd. All rights reserved.