Regioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8<i>H</i>)-trione with 2,4-hexadien-1-ol
No Thumbnail Available
Date
1999
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
The Diels-Alder reactions of 8,8-dimethylnaphtalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol and its O-acetyl derivative were investigated in different solvents. The regiochemistry of the cycloaddition of the hexadienol was determined through chemical correlation of one of the products. The solvent effect on the regioselectivity and endo/exo selectivity of this reaction is attributed to intermolecular hydrogen bonding between the hydroxyl group of the diene and the carbonyl oxygen atoms at C-4 and C-5 of the quinone in the transition state. The possible transition states have been modelled by AMI calculations in order to better interpret these experimental results. (C) 1998 Elsevier Science Ltd. All rights reserved.
Description
Keywords
Diels-Alder reactions, quinones, regiocontrol, hydrogen bonding