Reaction of trans-1,2-dichloroethylene with phosphorus trichloride–oxygen: the direct formation of a phosphate derivative from an olefin

Abstract

The reaction of trans-1,2-dichloroethylene with phosphorus trichloride–oxygen gives Cl₂P(:O)·O·CHCl·CHCl₂ as the major product (ca. 40% yield) and not the phosphonyl dichloride, Cl₂P(:O)·CHCl·CHCl₂, as previously reported. This is the first example of the direct formation of a phosphate derivative from an olefin. The phosphonyl dichloride is formed only in trace amounts together with two other minor products [Cl₂P(:O)·CHCl₂ and Cl₂P(:O)·O·CHCl₂] resulting from C–C cleavage of the olefin.