A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis beta-bromostyrenes

Authors
Kim, SH Wei, HX Willis, S Li, GG
Citation
Sh. Kim et al., A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis beta-bromostyrenes, SYN COMMUN, 29(23), 1999, pp. 4179-4185
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
23
Year of publication
1999
Pages
4179 - 4185
Database
ISI
SICI code
0039-7911(1999)29:23<4179:AMPFTS>2.0.ZU;2-E
Abstract
A new mild procedure has been developed for the synthesis of cis beta-bromo styrene analogs with complete Z/E selectivity and good to excellent yields (58.4 - 90.9%). The process involves carboxyl-halo-elimination of cinnamic acid dibromides by using triethylamine in N,N-dimethylformamide at room tem perature. A one-pot procedure has also been described for the direct transf ormation of cinnamic acids to beta-bromostyrenes.