The N-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool: Scope and Limitations

  1. Soldevilla, A. 1
  2. Sampedro, D. 1
  3. Campos, P.J. 1
  4. Rodríguez, M.A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of Organic Chemistry

ISSN: 0022-3263

Ano de publicación: 2005

Volume: 70

Número: 17

Páxinas: 6976-6979

Tipo: Artigo

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DOI: 10.1021/JO050871X PMID: 16095330 SCOPUS: 2-s2.0-23644459999 WoS: WOS:000231183000060 GOOGLE SCHOLAR

Outras publicacións en: Journal of Organic Chemistry

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Resumo

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.