Stable P-heterocyclic carbenes: scope and limitations.

Stable P-heterocyclic carbenes: scope and limitations. Research Abstract Details 

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Stable P-heterocyclic carbenes: scope and limitations. Abstract Text:

Jason D Masuda,David Martin,Celine Lyon-Saunier,Antoine Baceiredo,Heinz Gornitzka,Bruno Donnadieu,Guy Bertrand,

The conjugate acids (PHCH+s) of P-heterocyclic carbenes (PHCs) are prepared by formal [3+2] cycloaddition of a 1,3-diphosphaallyl or 1,3-phosphinophosphenium cation with various nitriles. The effect of the phosphorus substituent on the fate of the cyclization and on that of the counteranion and base in the subsequent deprotonation reaction are reported. Two PHCs that are indefinitely stable in the solid state are described. In solution, one of them, made from acetonitrile, undergoes a facile [3+2] cycloreversion, whereas the other, based on dimethyl cyanamide, is stable, presumably owing to its zwitterionic structure, which involves a tricoordinate pentavalent phosphorus atom. The reactivity of PHCs is strongly driven by the high electrophilicity of the phosphorus centers, as demonstrated by their reactivity with water and benzaldehyde. Although both PHCs reported in this paper are direct analogues of the least-basic NHCs, their basicity is comparable to those of the more strongly basic NHCs (as determined by comparison of the carbonyl stretching frequencies of their corresponding cis-[RhCl-(CO)2(L)] complexes).

Stable P-heterocyclic carbenes: scope and limitations. Publishing Authors By Initials

JD Masuda,D Martin,C Lyon-Saunier,A Baceiredo,H Gornitzka,B Donnadieu,G Bertrand,

For similar inorganic chemicals: phosphorus compounds: phosphines research abstracts see: inorganic chemicals: phosphorus compounds: phosphines research

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Stable P-heterocyclic carbenes: scope and limitations. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Chemistry, an Asian journal

VOLUME: 2

Page Numbers: 178-87

Journal Abbreviation:

ISSN: 1861-471X

DAY: 8

MONTH: Jan

YEAR: 2007

Stable P-heterocyclic carbenes: scope and limitations. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 101294643

Stable P-heterocyclic carbenes: scope and limitations. Keywords Mesh Terms:

KEYWORDS: Phosphines

MESH TERMS: chemistry

Chemical & Substance for Abstract: Stable P-heterocyclic carbenes: scope and limitations. Information

Substance Name: Methane

Registry Number: 74-82-8

Grant and Affiliation Information for Stable P-heterocyclic carbenes: scope and limitations.

AFFILIATION: UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA.

Country: Germany

AGENCY: United States NIGMS

GRANT: R01 GM 68825

ACRONYM: GM

MEDLINETA: Chem Asian J

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