Abstract
The reaction of 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole-5-carbonylchloride with phenylacetylene in benzene (80 °C) afforded 2-(2-chloro-2-phenylethenyl)-2,2-dichlorobenzo[d]-1,3,2-dioxaphosphole-5-carbonylchloride (yield >95%) as a result of the electrophilic 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.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 377–379, February, 2006.
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Mironov, V.F., Bogdanov, A.V. & Konovalov, A.I. Reaction of 2,2,2-trichlorobenzo[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-carbonylchloride. Russ Chem Bull 55, 390–392 (2006). https://doi.org/10.1007/s11172-006-0267-2
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DOI: https://doi.org/10.1007/s11172-006-0267-2