Unprecedented temperature-dependent formation of 3- and 7-methyl-3H-azepine derivatives by the reaction of o-nitrotoluene with tributylphosphine in nucleophilic media

Siti Mariyah Ulfa, Hideki Okamoto, Kyosuke Satake

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The reaction of o-methylphenylnitrene in the presence of alcohol and amine was expected to give isomeric pairs of 3- and 7-methyl-3H-azepine derivatives. The formation ratio between these isomers was found to be obviously influenced by reaction temperature, that is, reaction at 150°C gave 7-methyl-3Hazepine derivative, however, it became minor under 70°C in both media. The ratio between 3- and 7-methyl derivatives is explained by a scheme of kinetic- and thermodynamiccontrolled product distribution from o-methylphenylnitrene to 3- and 7-methyldehydroazepine intermediates which are trapped by nucleophilic media to give 3- and 7-methyl-3H-azepine derivatives.

Original languageEnglish
Pages (from-to)400-402
Number of pages3
JournalChemistry Letters
Volume41
Issue number4
DOIs
Publication statusPublished - Apr 24 2012

ASJC Scopus subject areas

  • Chemistry(all)

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