Reaction of benzylidenephenylsulfonylacetophenone with trimethyl phosphite and tris(dimethylamino) phosphine
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Benzylidenephenylsulfonylacetophenone (I) reacts with trimethyl phosphite (80°, C6H6) to give 2,2,2-trimethoxy-3,5-diphenyl-4-phenylsulfonyl-1,2-oxa-4-phospholene (II).
Two processes take place simultaneously at high temperatures (160°): isomerization of phosphorane (II) to give the dimethyl ester of 1,3-diphenyl-2-phenylsulfonyl-3-methoxy-2-propenephosphonic acid (VI), and decomposition of phosphorane (II) to the starting reactants with a cleavage of the P-C bond.
When phosphorane (II) is reacted with proton-donor reagents the phosphorane ring is opened at the P-O bond to give the dimethyl ester of 1-phenyl-2-benzoyl-2-phenylsulfonylethanephosphonic acid (III).
Benzylidenephenylsulfonylacetophenone (I) reacts with tris(dimethylamino)phosphine to give the 1∶1 adduct with a bipolar structure (VII) and containing the P-C bond. Its hydrolysis and reaction with dry HCl gas were studied.
KeywordsPhosphorane Ester Hydrolysis Adduct Dimethyl
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