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Communication | Regular issue | Vol 83, No. 6, 2011, pp.1259-1265
Published online, 11th April, 2011
DOI: 10.3987/COM-11-12172
Steric Effect on the Formation of 3H-Azepine Derivatives from o-Alkylphenylnitrene and Alcohol as a Nucleophilic Media

Siti Mariyah Ulfa, Hideki Okamoto, and Kyosuke Satake*

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


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.