Steric effect on the formation of 3H-azepine derivatives from o-alkylphenylnitrene and alcohol as a nucleophilic media

Siti Mariyah Ulfa, Hideki Okamoto, Kyosuke Satake

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The cause of regioselectivity for the formation of 3-alkyl- and/or 7-alkyl-3H-azepine derivatives via the intramolecular insertion reaction of o-alkylphenylnitrene, which is generated by an action of Bu3P on o-alkylnitrobenzene, in the presence of alcohol found to be elucidated by the steric effects of an alcohol adduct on the dehydroazepine intermediate. Observed selectivity is confirmed both by changing the bulkiness of the o-alkyl group of phenylnitrene and that of alcohol as a nucleophile.

Original languageEnglish
Pages (from-to)1259-1265
Number of pages7
JournalHeterocycles
Volume83
Issue number6
DOIs
Publication statusPublished - May 26 2011

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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