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The powerful effect of N-aryl substitution in promoting the thermal rearrangement of 5-spirocyclopropaneisoxazolidines

✍ Scribed by Franca M. Cordero; Ingrid Barile; Francesco De Sarlo; Alberto Brandi

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 239 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01339-8

No coin nor oath required. For personal study only.

✦ Synopsis

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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