Steric promotion of cyclization reactions: Substituent effect studies in the furan intramolecular Diels-Alder reaction

Authors
McNelis, BJ Starr, JT Dang, H
Citation
Bj. Mcnelis et al., Steric promotion of cyclization reactions: Substituent effect studies in the furan intramolecular Diels-Alder reaction, J HETERO CH, 35(6), 1998, pp. 1509-1513
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
35
Issue
6
Year of publication
1998
Pages
1509 - 1513
Database
ISI
SICI code
0022-152X(199811/12)35:6<1509:SPOCRS>2.0.ZU;2-J
Abstract
Seven alkyl and aryl substituted N-allyl-N-(methylfuran)-sulfonamide compou nds have been synthesized and their rates of cyclization and equilibrium pr oduct concentrations determined. Increased steric bulk on the sulfonamide s ubstituent has been shown to increase both the rate of cyclization and yiel ds of these reactions. A three-fold increase in rate and 15% increase in yi eld was observed as the substituent was varied from methyl to triisopropylb enzene.