New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines.

New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Research Abstract Details 

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New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Abstract Text:

Salvador Conejero,Maoying Song,David Martin,Yves Canac,Michele Soleilhavoup,Guy Bertrand,

Phosphonio-substituted aldiminium, iminium, and imidazolidinium salts are readily prepared by the addition of phosphines to the Alder dimer or by treatment of the corresponding chloroiminium salt with the phosphine/trimethylsilyl triflate adduct generated in situ. Reduction with either potassium metal or tetrakis(dimethylamino)ethylene leads to the corresponding C-amino phosphorus ylides. When basic phosphine fragments are used, the ylides can be isolated; otherwise they fragment into the carbene and phosphine. This method is limited to the preparation of transient carbenes, owing to the unavailability of sterically hindered dications, and consequently of phosphorus ylides with bulky carbon substituents. This difficulty is overcome by the addition of 2,4-di-tert-butyl-ortho-quinone to readily available C-amino phosphaalkenes at low temperature. Provided the phosphorus atom bears either an amino or tert-butyl group, [4+1] cycloaddition occurs, and the resulting ylides fragment into a dioxaphospholane and a spectroscopically observed carbene.

New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Publishing Authors By Initials

S Conejero,M Song,D Martin,Y Canac,M Soleilhavoup,G Bertrand,

For similar inorganic chemicals: elements: phosphorus research abstracts see: inorganic chemicals: elements: phosphorus research

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New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Chemistry, an Asian journal

VOLUME: 1

Page Numbers: 155-60

Journal Abbreviation:

ISSN: 1861-471X

DAY: 17

MONTH: Jul

YEAR: 2006

New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Information

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LANGUAGE: eng

NlmUniqueID: 101294643

New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Keywords Mesh Terms:

KEYWORDS: Phosphorus

MESH TERMS: chemistry

Chemical & Substance for Abstract: New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines. Information

Substance Name: phosphine

Registry Number: 7803-51-2

Grant and Affiliation Information for New synthetic routes to C-amino phosphorus ylides and their subsequent fragmentation into carbenes and phosphines.

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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