Synthesis and Properties of the Strained Alkene Perfluorobicyclo[2.2.0]hex-1(4)-ene

Synthesis and Properties of the Strained Alkene Perfluorobicyclo[2.2.0]hex-1(4)-ene

The title fluoroalkene has been generated by dehalogenation of dibromide and diiodide precursors and trapped in situ. retro-Diels–Alder reaction of its adduct with N-benzylpyrrole has made the alkene available in high yield and purity. In sharp contrast to its extremely labile hydrocarbon counterpar...

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Veröffentlicht in:Journal of organic chemistry 2015-02, Vol.80 (3), p.1523-1532
Hauptverfasser: Junk, Christopher P, He, Yigang, Zhang, Yin, Smith, Joshua R, Gleiter, Rolf, Kass, Steven R, Jasinski, Jerry P, Lemal, David M
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container_issue 3
container_start_page 1523
container_title Journal of organic chemistry
container_volume 80
creator Junk, Christopher P
He, Yigang
Zhang, Yin
Smith, Joshua R
Gleiter, Rolf
Kass, Steven R
Jasinski, Jerry P
Lemal, David M
description The title fluoroalkene has been generated by dehalogenation of dibromide and diiodide precursors and trapped in situ. retro-Diels–Alder reaction of its adduct with N-benzylpyrrole has made the alkene available in high yield and purity. In sharp contrast to its extremely labile hydrocarbon counterpart, the fluoroalkene is very stable yet highly reactive. Its characterization includes its electron affinity, photoelectron spectrum, and the previously reported structure determination by electron diffraction.
doi_str_mv 10.1021/jo502456h
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source ACS_美国化学学会期刊（与NSTL共建）
title Synthesis and Properties of the Strained Alkene Perfluorobicyclo[2.2.0]hex-1(4)-ene
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