Cycloaddition profile of pentafulvenes with 3-oxidopyrylium betaine: experimental and theoretical investigations |
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Authors: | Jinesh M. Kuthanapillil A. Nijamudheen Nayana Joseph Praveen Prakash E. Suresh Ayan Datta K.V. Radhakrishnan |
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Affiliation: | 1. National Institute for Interdisciplinary Science and Technology, CSIR (Formerly Regional Research Laboratory), Trivandrum 695019, Kerala, India;2. Department of Chemistry, St. Berchmans College, Changanacherry, Kottayam 686101, Kerala, India;3. Indian Association for the Cultivation of Science, 2A&2B Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India;4. Central Salt and Marine Chemicals Research Institute, Bhavnagar 364 002, India |
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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 [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. |
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Keywords: | Pentafulvenes 3-Oxidopyrylium betaine Microwave assisted reactions Cycloaddition Periselectivity |
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