The behaviour of isoxazolidinium salts with bases has been reconsidered. Exclusive formation of tetrahydro-1,3-oxazines occurs with 5,5-disubstituted derivatives. In the presence of a hydrogen atom at C-5 of the heterocycle, the competition of this reaction route with the Hofmann-like elimination leading to alpha,beta-enones has been established.

The behaviour of isoxazolidinium salts with bases has been reconsidered. Exclusive formation of tetrahydro-1,3-oxazines occurs with 5,5-disubstituted derivatives. In the presence of a hydrogen atom at C-5 of the heterocycle, the competition of this reaction route with the Hofmann-like elimination leading to alpha,beta-enones has been established.

COMPETITIVE FORMATION OF TETRAHYDRO-1,3-OXAZINES BY ISOXAZOLIDINIUM SALTS RING-OPENING REACTION

LIGUORI, Angelo;SINDONA, Giovanni
1991

Abstract

The behaviour of isoxazolidinium salts with bases has been reconsidered. Exclusive formation of tetrahydro-1,3-oxazines occurs with 5,5-disubstituted derivatives. In the presence of a hydrogen atom at C-5 of the heterocycle, the competition of this reaction route with the Hofmann-like elimination leading to alpha,beta-enones has been established.
The behaviour of isoxazolidinium salts with bases has been reconsidered. Exclusive formation of tetrahydro-1,3-oxazines occurs with 5,5-disubstituted derivatives. In the presence of a hydrogen atom at C-5 of the heterocycle, the competition of this reaction route with the Hofmann-like elimination leading to alpha,beta-enones has been established.
ALKALOIDS; N,O-HETEROCYCLICS; NITRONES
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/133512
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