The N-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool: Scope and Limitations
- Soldevilla, A. 1
- Sampedro, D. 1
- Campos, P.J. 1
- Rodríguez, M.A. 1
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1
Universidad de La Rioja
info
ISSN: 0022-3263
Año de publicación: 2005
Volumen: 70
Número: 17
Páginas: 6976-6979
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Journal of Organic Chemistry
Resumen
The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process. © 2005 American Chemical Society.