2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

Kiyoshi Matsumoto; Sadahito Goto; Naoto Hayashi; Hirokazu Iida; Takane Uchida; Akikazu Kakehi

doi:10.1002/ejoc.200400433

2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

Kiyoshi Matsumoto^*, Sadahito Goto, Naoto Hayashi, Hirokazu Iida, Takane Uchida, Akikazu Kakehi

^*Corresponding author for this work

Department of Chemistry

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

3 Scopus citations

Abstract

A 3-azabicyclo[3.2.0]hepta-1,4-diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β-position to give the ring-opened product, probably by a retro-Friedel-Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine.

Original language	English
Pages (from-to)	4667-4671
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	22
DOIs	https://doi.org/10.1002/ejoc.200400433
State	Published - 2004/11/12

Keywords

Azepine
Retro-Friedel - Crafts reaction
Ring opening
Small ring system

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200400433

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title = "2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate",

abstract = "A 3-azabicyclo[3.2.0]hepta-1,4-diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β-position to give the ring-opened product, probably by a retro-Friedel-Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine.",

keywords = "Azepine, Retro-Friedel - Crafts reaction, Ring opening, Small ring system",

author = "Kiyoshi Matsumoto and Sadahito Goto and Naoto Hayashi and Hirokazu Iida and Takane Uchida and Akikazu Kakehi",

year = "2004",

month = nov,

day = "12",

doi = "10.1002/ejoc.200400433",

language = "英語",

pages = "4667--4671",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "22",

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T1 - 2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

AU - Matsumoto, Kiyoshi

AU - Goto, Sadahito

AU - Hayashi, Naoto

AU - Iida, Hirokazu

AU - Uchida, Takane

AU - Kakehi, Akikazu

PY - 2004/11/12

Y1 - 2004/11/12

N2 - A 3-azabicyclo[3.2.0]hepta-1,4-diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β-position to give the ring-opened product, probably by a retro-Friedel-Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine.

AB - A 3-azabicyclo[3.2.0]hepta-1,4-diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β-position to give the ring-opened product, probably by a retro-Friedel-Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine.

KW - Azepine

KW - Retro-Friedel - Crafts reaction

KW - Ring opening

KW - Small ring system

UR - http://www.scopus.com/inward/record.url?scp=12344305443&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200400433

DO - 10.1002/ejoc.200400433

M3 - 学術論文

AN - SCOPUS:12344305443

SN - 1434-193X

SP - 4667

EP - 4671

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 22

ER -

2,3,4-Triphenyl-3-azabicyclo[3.2.0]hepta-1,4-diene - Facile ring-opening by electrophiles and novel reactions with dimethyl acetylenedicarboxylate

Abstract

Keywords

ASJC Scopus subject areas

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