Reactive intermediates. Part XX. Preparation of sulphoximides from sulphoxides and N-amino-lactams, and a study of their fragmentation
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1317-1321
- https://doi.org/10.1039/p19720001317
Abstract
Lead tetra-acetate oxidation of N-amino-lactams in the presence of sulphoxides gives sulphoximides in good yields. The sulphoximides undergo photochemical fragmentation to regenerate the sulphoxides and N-nitrenes, which can be intercepted by cyclohexene. Vapour phase pyrolysis at 400–500° also results in fragmentation of the sulphoximides, but under these conditions nitrogen is extruded from the heterocyclic systems, and products of ring contraction can be isolated. Thus, phthalimidosulphoximides give benzocyclobutene-1,2-dione.Keywords
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