Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

Zeguo Fang; Roscoe Z. Gillatt; Alexandra M. Z. Slawin; David B. Cordes; Cameron L. Carpenter-Warren; David O'Hagan

doi:10.1039/c9cc06426e

Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

Zeguo Fang, Roscoe Z. Gillatt, Alexandra M. Z. Slawin, David B. Cordes, Cameron L. Carpenter-Warren, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.

Original language	English
Pages (from-to)	14295-14298
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	95
Early online date	5 Nov 2019
DOIs	https://doi.org/10.1039/c9cc06426e
Publication status	Published - 11 Dec 2019

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10.1039/c9cc06426e

Unexpected alpha,alpha '-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene (dataset)
Gillatt, R. Z. (Creator), Slawin, A. M. Z. (Creator), Cordes, D. B. (Creator) & O'Hagan, D. (Creator), Cambridge Crystallographic Data Centre, 2019
https://dx.doi.org/10.5517/ccdc.csd.cc23cksv and 5 more links, https://dx.doi.org/10.5517/ccdc.csd.cc23cktw, https://dx.doi.org/10.5517/ccdc.csd.cc23ckvx, https://dx.doi.org/10.5517/ccdc.csd.cc23ckwy, https://dx.doi.org/10.5517/ccdc.csd.cc23ckxz, https://dx.doi.org/10.5517/ccdc.csd.cc23cky0 (show fewer)
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@article{888b3f0053c84b4da5eab202e11a5c1f,

title = "Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene",

abstract = "An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.",

author = "Zeguo Fang and Gillatt, {Roscoe Z.} and Slawin, {Alexandra M. Z.} and Cordes, {David B.} and Carpenter-Warren, {Cameron L.} and David O'Hagan",

note = "Authors thank the Chinese Scholarship Council for a studentship (ZF) and the EPSRC Mass Spectroscopy Service at Swansea for analysis.",

year = "2019",

month = dec,

day = "11",

doi = "10.1039/c9cc06426e",

language = "English",

volume = "55",

pages = "14295--14298",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "95",

}

TY - JOUR

T1 - Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

AU - Fang, Zeguo

AU - Gillatt, Roscoe Z.

AU - Slawin, Alexandra M. Z.

AU - Cordes, David B.

AU - Carpenter-Warren, Cameron L.

AU - O'Hagan, David

N1 - Authors thank the Chinese Scholarship Council for a studentship (ZF) and the EPSRC Mass Spectroscopy Service at Swansea for analysis.

PY - 2019/12/11

Y1 - 2019/12/11

N2 - An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.

AB - An unexpected and highly efficient reaction of dibenzo[a,e]cyclooctatetraene with Ag(I)F and N-bromosuccinamide in dichloromethane results in a sequential ring contraction pathway to generate bridged bicyclic α,α′-difluoroether isomers 10 and 11 where the ether oxygen is isotopically labelled from oxygen-18 water. In diethyl ether the same reaction generates the more classical vicinal difluoride isomers 13 and 14.

U2 - 10.1039/c9cc06426e

DO - 10.1039/c9cc06426e

M3 - Article

SN - 1359-7345

VL - 55

SP - 14295

EP - 14298

JO - Chemical Communications

JF - Chemical Communications

IS - 95

ER -

Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

Abstract

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Unexpected alpha,alpha '-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene (dataset)

Cite this