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Report | Regular issue | Vol 22, No. 6, 1984, pp.1369-1375
Published online, 1st January, 1970
DOI: 10.3987/R-1984-06-1369
Addition of Phthalimido Nitrene to Substituted Cyclopentadienes

Krishna Narasimhan* and Perumal Raja Kumar

*Department of Organic Chemistry, Guindy Campus, University of Madras, Chennai-600 025, India

Abstract

The aziridines 3,3a and 3b obtained by the cycloaddition of phthalimidonitrene to cyclopentadiene derivatives 2, 2a and 2b undergoes facile ring expansion, when treated with sodium hydride to give substituted pyridine derivatives 4, 4a and 4b respectively. Hydrazinolysis of the aziridines gives the cyclopentadiene derivatives through the intermediacy of N-aminoaziridines 5,5a and 5b. Oxidation of the aziridines 3,3a with lead tetraacetate gives ths aziridine 6 and 6a.