Cycloaddition profile of pentafulvenes with 3-oxidopyrylium betaine: Experimental and theoretical investigations. K
No Thumbnail Available
Date
2013-09-13
Journal Title
Journal ISSN
Volume Title
Publisher
elsevier
Abstract
A detailed investigation on the effect of solvent polarity, temperature, and microwave irradiation on
periselectivity in cycloaddition reactions of pentafulvenes with 3-oxidopyrylium betaine is described.
The base catalyzed generation of 3-oxidopyrylium betaine in CHCl3 resulted in the exclusive formation of
[6þ3] adducts. With increase in solvent polarity and temperature, mixtures of [6þ3] and [3þ2] adducts
were formed, where as under microwave irradiation, [3þ2] adducts were formed exclusively. The
experimental results have been rationalized on the basis of theoretical calculations.
Description
Keywords
Pentafulvenes, 3-Oxidopyrylium betaine, Microwave assisted reactions, Cycloaddition, Periselectivity