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

Fingerprint

Azepines
Alcohols
Derivatives
Regioselectivity
Nucleophiles

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Steric effect on the formation of 3H-azepine derivatives from o-alkylphenylnitrene and alcohol as a nucleophilic media. / Ulfa, Siti Mariyah; Okamoto, Hideki; Satake, Kyosuke.

In: Heterocycles, Vol. 83, No. 6, 26.05.2011, p. 1259-1265.

Research output: Contribution to journalArticle

@article{100fceaa7d504fd19d0f64ec9b7da16a,
title = "Steric effect on the formation of 3H-azepine derivatives from o-alkylphenylnitrene and alcohol as a nucleophilic media",
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.",
author = "Ulfa, {Siti Mariyah} and Hideki Okamoto and Kyosuke Satake",
year = "2011",
month = "5",
day = "26",
doi = "10.3987/COM-11-12172",
language = "English",
volume = "83",
pages = "1259--1265",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "6",

}

TY - JOUR

T1 - Steric effect on the formation of 3H-azepine derivatives from o-alkylphenylnitrene and alcohol as a nucleophilic media

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 - http://www.scopus.com/inward/record.url?scp=79957657934&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79957657934&partnerID=8YFLogxK

U2 - 10.3987/COM-11-12172

DO - 10.3987/COM-11-12172

M3 - Article

AN - SCOPUS:79957657934

VL - 83

SP - 1259

EP - 1265

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 6

ER -