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Abstract
The reaction of the isomeric phosphites, 1 and 2, with ozone have been shown to be stereospecific and to proceed with retention of configuration about phosphorus. Similarly ozonization of mixtures of 3 and 4 were found to be stereospecific or very nearly so with retention of configuration about phosphorus. The mechanistic implications of these findings are discussed. Reactions of 1 and 2 with neopentyl and t-butyl hypochlorites proceed in a stereochemically random manner. The formation of a pentacoordinated intermediate is implicated. Reactions of a mixture of 1 and 2 with ethyl thiyl radicals provided phosphorothionates with complete retention of configuration.