Frontispiece: Stepwise Reduction of an α-Phosphonio-Carbocation to a Crystalline Phosphorus Radical Cation and an Acridinyl-Phosphorus Ylide

Organo‐Main Group Derivatives The discovery of the Wittig reaction in 1954 has led to intensive research into the chemistry of phosphorus ylides over the past decades. While the redox chemistry of ylides was investigated in the late 1990s, now, twenty years later, in their Communication on page 2882...

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Published inChemistry : a European journal Vol. 22; no. 9; pp. np - n/a
Main Authors Hudnall, Todd W., Dorsey, Christopher L., Jones, James S., Gabbaï, François P.
Format Journal Article
LanguageEnglish
Published Blackwell Publishing Ltd 24.02.2016
Subjects
Bonding
carbocation
Cations
Crystal structure
Derivatives
main group elements
Phosphorus
radical
Radicals
Reduction
ylide
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Summary:Organo‐Main Group Derivatives The discovery of the Wittig reaction in 1954 has led to intensive research into the chemistry of phosphorus ylides over the past decades. While the redox chemistry of ylides was investigated in the late 1990s, now, twenty years later, in their Communication on page 2882 ff., the groups of Hudnall and Gabbaï demonstrate for the first time that stable α‐phosphonio‐carbocations, the fully oxidized form of phosphorus ylides, can be synthesized. This dication can be reduced by one electron to afford a stable radical cation that features a one‐electron P−C π bond, or by two electrons to give the corresponding antiaromatic phosphorus ylide.
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ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201680961