Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

Aki Kohyama; Eri Koresawa; Kiyoshi Tsuge; Yuji Matsuya

doi:10.1039/c9cc01679a

Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

Aki Kohyama, Eri Koresawa, Kiyoshi Tsuge, Yuji Matsuya^*

^*Corresponding author for this work

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

12 Scopus citations

Abstract

Electron-donating iminophosphoranes were found to significantly enhance 4π-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20-25 °C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reaction-triggered sequential molecular transformations of the azide benzocyclobutenes have been established via o-quinodimethanes at ambient temperature, which is expected to exhibit potential for a wide range of applications.

Original language	English
Pages (from-to)	6205-6208
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	44
DOIs	https://doi.org/10.1039/c9cc01679a
State	Published - 2019

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c9cc01679a

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title = "Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature",

abstract = "Electron-donating iminophosphoranes were found to significantly enhance 4π-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20-25 °C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reaction-triggered sequential molecular transformations of the azide benzocyclobutenes have been established via o-quinodimethanes at ambient temperature, which is expected to exhibit potential for a wide range of applications.",

author = "Aki Kohyama and Eri Koresawa and Kiyoshi Tsuge and Yuji Matsuya",

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doi = "10.1039/c9cc01679a",

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T1 - Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

AU - Kohyama, Aki

AU - Koresawa, Eri

AU - Tsuge, Kiyoshi

AU - Matsuya, Yuji

PY - 2019

Y1 - 2019

N2 - Electron-donating iminophosphoranes were found to significantly enhance 4π-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20-25 °C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reaction-triggered sequential molecular transformations of the azide benzocyclobutenes have been established via o-quinodimethanes at ambient temperature, which is expected to exhibit potential for a wide range of applications.

AB - Electron-donating iminophosphoranes were found to significantly enhance 4π-ring opening of benzocyclobutenes to generate o-quinodimethanes at 20-25 °C. These iminophosphorane benzocyclobutenes can be conveniently generated from azide benzocyclobutenes and phosphines via the Staudinger reaction. Thus, Staudinger reaction-triggered sequential molecular transformations of the azide benzocyclobutenes have been established via o-quinodimethanes at ambient temperature, which is expected to exhibit potential for a wide range of applications.

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JO - Chemical Communications

JF - Chemical Communications

IS - 44

ER -

Facile o-quinodimethane formation from benzocyclobutenes triggered by the Staudinger reaction at ambient temperature

Abstract

ASJC Scopus subject areas

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