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
1991-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
