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The N-cyclopropylimine-1-pyrroline photorearrangement as a synthetic tool: scope and limitations.

Authors
  • Soldevilla, Alberto
  • Sampedro, Diego
  • Campos, Pedro J
  • Rodríguez, Miguel A
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Aug 19, 2005
Volume
70
Issue
17
Pages
6976–6979
Identifiers
PMID: 16095330
Source
Medline
License
Unknown

Abstract

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.

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