USE OF 3,3'-POLYMETHYLENE-BRIDGED THIAZOLIUM SALTS PLUS BASES AS CATALYSTS OF THE BENZOIN CONDENSATION AND ITS MECHANISTIC IMPLICATIONS - PROPOSAL OF A NEW MECHANISM IN APROTIC CONDITIONS

Authors
LOPEZCALAHORRA F CASTELLS J DOMINGO L MARTI J BOFILL JM
Citation
F. Lopezcalahorra et al., USE OF 3,3'-POLYMETHYLENE-BRIDGED THIAZOLIUM SALTS PLUS BASES AS CATALYSTS OF THE BENZOIN CONDENSATION AND ITS MECHANISTIC IMPLICATIONS - PROPOSAL OF A NEW MECHANISM IN APROTIC CONDITIONS, Heterocycles, 37(3), 1994, pp. 1579-1597
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
3
Year of publication
1994
Pages
1579 - 1597
Database
ISI
SICI code
0385-5414(1994)37:3<1579:UO3TSP>2.0.ZU;2-#
Abstract
3,3'-Polymethylene-bridged thiazolium and benzothiazolium salts are us ed as precatalysts for the benzoin condensation and it is found that c atalytic activity depends strongly on the methylene bridge length. Thi s result supports our previous postulation that, at least in strictly aprotic medium, bis(thiazolin-2-ylidene)s, and not thiazolin-2-ylidene s, are the catalytic species in the benzoin condensation catalyzed hy thiazolium salts plus base. As a consequence, a new mechanism based in experimental data and AM1 calculations is proposed.