N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone derivatives by heating. The presence of a phcnyl ring on th¢ nitrogen atom significantly reduces th¢ rearrangement temperature. This effect is enhanced by electrondonating substitucnts and reduced by electron-withdrawing substituents on the phenyl ring.
The Powerful Effect of N-Aryl Substitution in Promoting theThermal Rearrangement of 5-Spirocyclopropaneisoxazolidines / F. M. Cordero; I. Barile; F. De Sarlo; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 40:(1999), pp. 6657-6660.
The Powerful Effect of N-Aryl Substitution in Promoting theThermal Rearrangement of 5-Spirocyclopropaneisoxazolidines
CORDERO, FRANCA MARIA;DE SARLO, FRANCESCO;BRANDI, ALBERTO
1999
Abstract
N-Alkyl 5-spirocyclopropaneisoxazolidines rearrange to tetrahydropyridone derivatives by heating. The presence of a phcnyl ring on th¢ nitrogen atom significantly reduces th¢ rearrangement temperature. This effect is enhanced by electrondonating substitucnts and reduced by electron-withdrawing substituents on the phenyl ring.
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