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

4 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 - May 26 2011

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-11-12172

Cite this

@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 = may,

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

SN - 0385-5414

VL - 83

SP - 1259

EP - 1265

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this