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Oxidative Cyclization of Unsaturated Ketene Dithioacetals with Ceric Ammonium Nitrate to Form Bicyclic Lactones
Journal article   Peer reviewed

Oxidative Cyclization of Unsaturated Ketene Dithioacetals with Ceric Ammonium Nitrate to Form Bicyclic Lactones

Barry B Snider, Bo Shi and Cheri A Quickley
Tetrahedron, Vol.56(52), pp.10127-10132
12/22/2000

Abstract

cation-like cyclization bicyclic lactones ceric ammonium nitrate
Ceric ammonium nitrate oxidizes unsaturated ketene dithioacetals in wet MeCN to give cation radicals that cyclize to trisubstituted double bonds and styrenes by cation-like cyclizations leading to cyclic cation radicals that are transformed by further oxidation, hydrolysis and cyclization to bicyclic lactones in moderate to good yield.

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