期刊
TETRAHEDRON
卷 69, 期 46, 页码 9751-9760出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.09.016
关键词
Pentafulvenes; 3-Oxidopyrylium betaine; Microwave assisted reactions; Cycloaddition; Periselectivity
资金
- UGC
- CSIR, New Delhi
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 [6+3] adducts. With increase in solvent polarity and temperature, mixtures of [6+3] and [3+2] adducts were formed, where as under microwave irradiation, [3+2] adducts were formed exclusively. The experimental results have been rationalized on the basis of theoretical calculations. (C) 2013 Elsevier Ltd. All rights reserved.
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