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Unusual Tandem Oxidative C-C Bond Cleavage and Acetalization of Chalcone Epoxides in the Presence of Iodine in Methanol

Balaso G. Jadhav, Shriniwas D. Samant*

*Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai 400019, India, Email: sd.samantictmumbai.edu.in

B. G. Jadhav, S. D. Samant, Synlett, 2014, 25, 1591-1595.

DOI: 10.1055/s-0033-1339134 (free Supporting Information)


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Abstract

Chalcone epoxides form α,α-dimethoxyacetophenones on heating with iodine in methanol through C-C bond cleavage followed by acetalization of the formyl group. The process occurs through ring opening of the chalcone epoxide by methanol to form β-methoxy alcohol, cleavage of the C-C bond in the latter to form α-ketoaldehyde, and acetalization of the formyl group to give the product.

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Key Words

oxidative cleavage, chalcone epoxides, iodine, α,α-dimethoxyacetophenones, acetals, α-ketoaldehydes


ID: J60-Y2014