Alkyne mechanochemistry: Putative activation by transoidal bending

Charles E. Diesendruck; Lingyang Zhu; Jeffrey S. Moore

doi:https://doi.org/10.1039/c4cc03514c

Alkyne mechanochemistry: Putative activation by transoidal bending

Charles E. Diesendruck, Lingyang Zhu, Jeffrey S. Moore

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

Abstract

We investigated the use of mechanical stress to bend carbon-carbon triple bonds. Formation of an isoquinoline after reaction with a benzyl azide trap points towards a nucleophilic addition mechanism, differentiating mechanochemical trans-bending of π bonds from the typical reactivity observed for cisoidal bending of triple bonds in strained cyclic alkynes.

Original language	American English
Pages (from-to)	13235-13238
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	87
DOIs	https://doi.org/10.1039/c4cc03514c
State	Published - 11 Nov 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

Access to Document

https://doi.org/10.1039/c4cc03514c

Cite this

@article{c05422104363453780a201498ad8418a,

title = "Alkyne mechanochemistry: Putative activation by transoidal bending",

abstract = "We investigated the use of mechanical stress to bend carbon-carbon triple bonds. Formation of an isoquinoline after reaction with a benzyl azide trap points towards a nucleophilic addition mechanism, differentiating mechanochemical trans-bending of π bonds from the typical reactivity observed for cisoidal bending of triple bonds in strained cyclic alkynes.",

author = "Diesendruck, {Charles E.} and Lingyang Zhu and Moore, {Jeffrey S.}",

note = "Publisher Copyright: {\textcopyright} 2014 the Partner Organisations.",

year = "2014",

month = nov,

day = "11",

doi = "https://doi.org/10.1039/c4cc03514c",

language = "American English",

volume = "50",

pages = "13235--13238",

number = "87",

}

TY - JOUR

T1 - Alkyne mechanochemistry

T2 - Putative activation by transoidal bending

AU - Diesendruck, Charles E.

AU - Zhu, Lingyang

AU - Moore, Jeffrey S.

PY - 2014/11/11

Y1 - 2014/11/11

N2 - We investigated the use of mechanical stress to bend carbon-carbon triple bonds. Formation of an isoquinoline after reaction with a benzyl azide trap points towards a nucleophilic addition mechanism, differentiating mechanochemical trans-bending of π bonds from the typical reactivity observed for cisoidal bending of triple bonds in strained cyclic alkynes.

AB - We investigated the use of mechanical stress to bend carbon-carbon triple bonds. Formation of an isoquinoline after reaction with a benzyl azide trap points towards a nucleophilic addition mechanism, differentiating mechanochemical trans-bending of π bonds from the typical reactivity observed for cisoidal bending of triple bonds in strained cyclic alkynes.

UR - http://www.scopus.com/inward/record.url?scp=84929208018&partnerID=8YFLogxK

U2 - https://doi.org/10.1039/c4cc03514c

DO - https://doi.org/10.1039/c4cc03514c

M3 - Article

SN - 1359-7345

VL - 50

SP - 13235

EP - 13238

JO - Chemical Communications

JF - Chemical Communications

IS - 87

ER -

Alkyne mechanochemistry: Putative activation by transoidal bending

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Cite this