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Title: Cycloaddition profile of pentafulvenes with 3-oxidopyrylium betaine: Experimental and theoretical investigations. K
Authors: Kuthanapillil, Jinesh M
Nijamudheen, A.
Joseph, Nayana
Prakash, Praveen
Suresh, E
Datta, Ayan
Radhakrishnan, K V
Keywords: Pentafulvenes
3-Oxidopyrylium betaine
Microwave assisted reactions
Issue Date: 13-Sep-2013
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.
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