Novel perfluoroacyl olefinations of aldehydes using beta-thio-substituted perfluoroalkyl enol ethers

Authors
Yoshimatsu, M Sugimoto, T Okada, N Kinoshita, S
Citation
M. Yoshimatsu et al., Novel perfluoroacyl olefinations of aldehydes using beta-thio-substituted perfluoroalkyl enol ethers, J ORG CHEM, 64(14), 1999, pp. 5162-5165
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
14
Year of publication
1999
Pages
5162 - 5165
Database
ISI
SICI code
0022-3263(19990709)64:14<5162:NPOOAU>2.0.ZU;2-R
Abstract
alpha-(Methylthio)- or alpha-(phenylthio)-substituted perfluaroacylolefinat ions of nonenolizable aldehydes using the beta-lithio-beta-thio-perfluoroal kyl enol ethers 1-4 stereoselectively proceeded to give (Z)-alpha,beta-unsa turated perfluoroalkyl ketones 9a-e, 10a-c, 11a-c, and 12a. The alpha-(thio )-alpha,beta-unsaturated trifluoromethyl ketones were easily converted to 3 -(thio)-2-(trifluoromethyl)-1,3-butadienes 21a-c and 22a,b in moderate to h igh yields (41-85%).