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.

Cycloaddition reactions of N-phenylsulfonyl-1-azabuta-1,3-dienes with mesoionic 2,4-diphenyl-1-methyl-1,3-oxazolium 5-oxide / P. Dalla Croce, R. Ferraccioli, C. La Rosa, T. Pilati. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - :8(1993), pp. 1511-1515.

Cycloaddition reactions of N-phenylsulfonyl-1-azabuta-1,3-dienes with mesoionic 2,4-diphenyl-1-methyl-1,3-oxazolium 5-oxide

P. Dalla Croce
Primo
;
C. La Rosa
Penultimo
;
1993

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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/192130
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