Cycloaddition reactions of N-phenylsulfonyl-1-azabuta-1,3-dienes with mesoionic 2,4-diphenyl-1-methyl-1,3-oxazolium 5-oxide
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 1511-1515
- https://doi.org/10.1039/p29930001511
Abstract
N-Phenylsulfonyl unsaturated imines (1) react with 2,4-diphenyl-3-methyl-1,3-oxazolium 5-oxide (2) giving 4-styrylimidazoles (3), open chain products (4) and pyrrol-3-ylcarboxaldehyde N-phenylsulfonylimines (5). The mechanism of formation of all the products as well as the different behaviour of imines 1 compared with those lacking the N-tosyl group are discussed. The structures have been assigned on the basis of 1H NMR evidence and by X-ray analysis.Keywords
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