Issue 5, 2016

From the parent phosphinidene–carbene adduct NHC[double bond, length as m-dash]PH to cationic P4-rings and P2-cycloaddition products

Abstract

Reactions of the parent phosphinidene–carbene adduct DippNHC[double bond, length as m-dash]PH with chlorophosphanes are reported herein. The obtained DippNHC-substituted chlorodiphosphanes, DippNHC[double bond, length as m-dash]P–PClR, and the formation of their cationic derivatives, [DippNHC–P[double bond, length as m-dash]PR]+, were also explored. Depending on the steric demand of their substituents, these cations were found to be monomeric [DippNHC–PP–NiPr2][GaCl4] or to dimerise to cyclotetraphosphanes [DippNHC–PP–R]2[GaCl4]2 (R = Ph, NMe2). For R = NMe2, this dication is the first isolated example of a tetrasubstituted all-σ3 cyclotetraphosphane. Finally, the hetero-Diels–Alder reactivity of these cations was studied with 2,3-dimethylbuta-1,3-diene and cyclopentadiene, resulting in the isolation of a number of cationic 1,2-diphosphinanes.

Graphical abstract: From the parent phosphinidene–carbene adduct NHC [[double bond, length as m-dash]] PH to cationic P4-rings and P2-cycloaddition products

Supplementary files

Article information

Article type
Paper
Submitted
05 août 2015
Accepted
14 sept. 2015
First published
23 sept. 2015

Dalton Trans., 2016,45, 2044-2052

Author version available

From the parent phosphinidene–carbene adduct NHC[double bond, length as m-dash]PH to cationic P4-rings and P2-cycloaddition products

A. Beil, R. J. Gilliard and H. Grützmacher, Dalton Trans., 2016, 45, 2044 DOI: 10.1039/C5DT03014E

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