Abnormal effect of Gn(2)SO(4) as compared to other guanidinium salts on rates and stereoselectivities of Diels-Alder reactions

Authors
Kumar, A Pawar, SS
Citation
A. Kumar et Ss. Pawar, Abnormal effect of Gn(2)SO(4) as compared to other guanidinium salts on rates and stereoselectivities of Diels-Alder reactions, TETRAHEDR L, 42(49), 2001, pp. 8681-8683
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
49
Year of publication
2001
Pages
8681 - 8683
Database
ISI
SICI code
0040-4039(200112)42:49<8681:AEOGAC>2.0.ZU;2-6
Abstract
An abnormal effect in that guanidinium sulphate increases the rates and end o product formation of the reaction of cyclopentadiene with methyl acrylate is recorded for the first time in Diels-Alder chemistry. Other guanidinium salts like chloride, bromide, acetate and perchlorate inhibit the reaction rates and give rise to more exo products. This contrasting effect of Gn(2) SO(4) on the kinetics of the Diels-Alder reaction can be attributed to the dominant role of SO42- over the guanidinium cation. (C) 2001 Elsevier Scien ce Ltd. All rights reserved.