STEREOSPECIFIC FORMATION OF 2-[(E)-ALK-1'-ENYL] BENZOIC-ACIDS IN AN UNUSUAL REACTION OF THIOPHTHALIDES WITH ALDEHYDES

Authors
MAL D MAJUMDAR G PAL R
Citation
D. Mal et al., STEREOSPECIFIC FORMATION OF 2-[(E)-ALK-1'-ENYL] BENZOIC-ACIDS IN AN UNUSUAL REACTION OF THIOPHTHALIDES WITH ALDEHYDES, Journal of the Chemical Society. Perkin transactions. I, (9), 1994, pp. 1115-1116
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
9
Year of publication
1994
Pages
1115 - 1116
Database
ISI
SICI code
0300-922X(1994):9<1115:SFO2BI>2.0.ZU;2-R
Abstract
The reaction of thiophthalides 1 with aldehydes 3 in the presence of l ithium tert-butoxide at -60 to 25 degrees C results in the stereospeci fic formation of only trans 2-(alk-1'-enyl)benzoic acids 4 in fairly g ood yields in one-pot operations. This reaction is proposed to proceed via episulfide formation followed by sulfur extrusion, and corroborat ed by an unprecedented reaction of phthalide with thiobenzophenone giv ing the acid 11a under similar conditions.