The Wittig reaction of ethyl (triphenylphosphoranylidene)acetate (2a) with the carbonyl group of trisubstituted 5(4H)-oxazolones 1a–c afforded ethyl 5(4H)-oxazolylideneacetates 3a–c and triphenylphosphane oxide. Starting from oxazolones 1d–i and ylide 2a, methyleneoxazoles 3d, e and ethyl 5-oxazoleacetates 4a–f were obtained besides ylides 5a–e deriving from the nucleophilic attack of the ylide at 1 and subsequent opening of the oxazole ring. Oxazolones 1a–c reacted also with triphenylphosphonium phenylmethylide (2b) to yield methyleneoxazoles 3f,g and ylides 5f–h. By treating triphenylphosphonium methylide (2c) and -methoxymethylide (2d) with 1a–c only open-chain compounds 5i–k and 5l–n, respectively, were obtained.

5‐Oxazolones, IV. Reactions of 5(4H)‐oxazolones with triphenylphosphonium methylides / E. Erba, M.L. Gelmi, D. Pocar. - In: CHEMISCHE BERICHTE-RECUEIL. - ISSN 0009-2940. - 121:8(1988), pp. 1519-1524. [10.1002/cber.19881210828]

5‐Oxazolones, IV. Reactions of 5(4H)‐oxazolones with triphenylphosphonium methylides

E. Erba
Primo
;
M.L. Gelmi
Secondo
;
D. Pocar
Ultimo
1988

Abstract

The Wittig reaction of ethyl (triphenylphosphoranylidene)acetate (2a) with the carbonyl group of trisubstituted 5(4H)-oxazolones 1a–c afforded ethyl 5(4H)-oxazolylideneacetates 3a–c and triphenylphosphane oxide. Starting from oxazolones 1d–i and ylide 2a, methyleneoxazoles 3d, e and ethyl 5-oxazoleacetates 4a–f were obtained besides ylides 5a–e deriving from the nucleophilic attack of the ylide at 1 and subsequent opening of the oxazole ring. Oxazolones 1a–c reacted also with triphenylphosphonium phenylmethylide (2b) to yield methyleneoxazoles 3f,g and ylides 5f–h. By treating triphenylphosphonium methylide (2c) and -methoxymethylide (2d) with 1a–c only open-chain compounds 5i–k and 5l–n, respectively, were obtained.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/182604
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