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

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
, Kyosuke Satake

Research output: Contribution to journal › Article › peer-review

5 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 language	English
Pages (from-to)	1259-1265
Number of pages	7
Journal	Heterocycles
Volume	83
Issue number	6
DOIs	https://doi.org/10.3987/COM-11-12172
Publication status	Published - 26 May 2011
Externally published	Yes

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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.",

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AU - Ulfa, Siti Mariyah

AU - Okamoto, Hideki

AU - Satake, Kyosuke

PY - 2011/5/26

Y1 - 2011/5/26

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/79957657934

U2 - 10.3987/COM-11-12172

DO - 10.3987/COM-11-12172

M3 - Article

AN - SCOPUS:79957657934

SN - 0385-5414

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JO - Heterocycles

JF - Heterocycles

IS - 6

ER -

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

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