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Communication | Regular issue | Vol 12, No. 1, 1979, pp.5-10
Published online, 1st January, 1970
DOI: 10.3987/R-1979-01-0005
1,3-Dipolar Cycloreversions of Isoxazolidines and Pyrazolidines

Remo Gandolfi,* Lucio Toma, and Carlo De Micheli

*Dipartamento di Chimica Organica, Università di Pavia, V. le Taramelli 10, 27100 Pavia, Italy


1,3-Dipolar cycloreversion reactions of the adducts of 3,4-dihydroisoquinoline-N-oxide and of 3,4-dihydroisoquinoline-N-phenylimine with cyclic α,β-unsaturated ketones and their ethylene ketals were investigated. The easier fragmentation of the adducts with α,β-unsaturated ketones compared with that of the corresponding ketals can be explained on the basis of conjugation gain in the cycloreversion transition state of the former compounds.