Reaction of 2,2,2-trichIorobenzo[d]-1,3,2-dioxaphosphole-5-carbonylchloride with phenylacetylene: predominant formation of 2-(2-chloro-2-phenylethenyl)-2,2-dichlorobenzo[d] -1,3,2-dioxaphosphole-5-carl)onylchloride

摘要

The reaction of 2,2,2-trichlorobenzo[d]-l,3,2-dioxaphosphole-5-carbonylchloride with phenylacetylene in benzene (80 deg C) afforded 2-(2-chloro-2-phenylethenyl)-2,2-dichloro-benzo[d]-l,3,2-dioxaphosphole-5-carbonylchloride (yield >95%) as a result of the electro-philic cis-addition of the phosphorus(v) derivative at the triple bond of acetylene with retention of coordination of the P atom.Hydrolysis of this compound affords predominantly 2-hydroxy-5-(hydroxycarbonyl)phenyl (2-chloro-2-phenylethenyl)phosphonate.