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.