1,3 Dipolar cycloaddition of C-benzoyl-N-phenylnitrone to esters of vinyl-, β-cyanovinyl, and allylphosphosphonic acids and of C,N-diphenylnitrone to an allylphosphonic acid ester

Research paper by B. A. Arbuzov, Yu. Yu. Samitov, É. N. Dianova, A. F. Lisin

Indexed on: 01 Dec '76Published on: 01 Dec '76Published in: Russian Chemical Bulletin


The reaction of 1,3 dipolar cycloaddition of C-benzoyl-N-phenylnitrone to dimethyl vinylphosphonate at 20° gave isomeric trans-2-phenyl-3-benzoyl-4-dimethylphosphono- and trans-2-phenyl-3-benzoyl-5-dimethylphosphonoixoxazolidines. Only the first isomer is obtained in the reaction in boiling benzene.The 1,3 dipolar addition of C-benzoyl-N-phenylnitrone to the diethyl ester of β-cyanovinylphosphonic acid leads to trans-2-phenyl-3-benzoyl-4-diethylphosphono-5-cyanoisoxazolidine.The cycloaddition of C,N-diphenylnitrone to the dimethyl ester of allylphosphonic acid leads to the formation of trans-2,3-diphenyl-5-dimethylphosphonomethyleneisoxazolidine, while the cycloaddition of C-benzoyl-N-phenylnitrone to this diester gives trans-2-phenyl-3-benzoyl-5-dimethylphosphonomethyleneisoxazolidine.