Conclusions
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1.
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.
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2.
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.
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3.
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.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2779–2785, December, 1976.
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Arbuzov, B.A., Samitov, Y.Y., Dianova, É.N. et al. 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. Russ Chem Bull 25, 2589–2594 (1976). https://doi.org/10.1007/BF00920904
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DOI: https://doi.org/10.1007/BF00920904