CALIX[4]ARENE SULFONATES - PALLADIUM-CATALYZED INTERMOLECULAR MIGRATION OF SULFONYL GROUPS AND ISOLATION OF A CALIX[4]ARENE IN A CHIRAL 1,2-ALTERNATE CONFORMATION

Citation
Jj. Gonzalez et al., CALIX[4]ARENE SULFONATES - PALLADIUM-CATALYZED INTERMOLECULAR MIGRATION OF SULFONYL GROUPS AND ISOLATION OF A CALIX[4]ARENE IN A CHIRAL 1,2-ALTERNATE CONFORMATION, Journal of organic chemistry, 60(23), 1995, pp. 7419-7423
Citations number
83
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
60
Issue
23
Year of publication
1995
Pages
7419 - 7423
Database
ISI
SICI code
0022-3263(1995)60:23<7419:CS-PIM>2.0.ZU;2-L
Abstract
An intermolecular migration of sulfonyl groups in 1,3-bistriflate and 1,3-bismesylate derivatives of p-tert-butylcalix[4]arene (1) takes pla ce in the presence of both a palladium catalyst and chloride anion. Th e process leads to the clean formation of 1:1 mixtures of mono- and tr isubstituted derivatives that could not be prepared directly from 1 by sulfonylation reactions. A trismesylate 7b is obtained as a minor der ivative under the conditions required for the mesylation of 1. Compoun d 7b exists in a 1,2-alternate conformation, which is chiral due to th e pattern of substituents.