Abstract
Abstract In contrast to difficultly characterizable products of olefins with P4S10 alone, the reactions of olefins with P4S10 in the presence of PSCI3 (and in some cases, PCl3) afforded distillable products amenable to characterization. Ethylene with P4S10, PSCl3, and PCl3 gave 1,2-ethanediylbis (phosphonothioic dichloride) in good yield. Propylene with P4S10 and PSCl3 afforded several open-chain phosphonothioic chlorides and at higher temperatures 2-chloro-1,2-thiaphospholane 2-sulfide. 1- or 2-Butene yielded the 5-methyl homolog. Cyclohexene yielded 7-chloro-6-thia-7-phosphabicyclo [3.2.1] octane 7-sulfide and 4-methylcyclohexene yielded the 5-methyl homolog. Norbornene gave stereoisomeric 3-chloro-2-thia-3-phosphatricyclo [4.3.0.04,8] nonane 3-sulfides. Norbornadiene gave 3-chloro-2-thia-3-phosphatricyclo [4.3.0.04,8] non-6-ene 3-sulfide. Camphene reacted with P4S10 and PSCl3 in good yield at ambient pressure and moderate heating to produce a characteristic Wagner-Meerwein rearrangement product, 3-chlo...
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