Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes.

Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Research Abstract Details 

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Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Abstract Text:

Only basic phosphines, such as tris(dimethylamino)phosphine, allow for the synthesis of a stable acyclic beta-amino phosphonium salt 1c, which upon deprotonation with butyllithium affords the corresponding stable C-amino phosphorus ylide 2c. In contrast, cyclic beta-amino phosphonium salts 5a and 5b are stable despite the presence of weakly basic triarylphosphine fragments. They are prepared by intramolecular insertion of the carbene center of (amino)(phosphonio)carbenes into the CH bond of a phosphorus substituent. Deprotonation of 5a leads to the corresponding cyclic C-amino phosphorus ylide 6a, which has been fully characterized including an X-ray diffraction study. Deprotonation of 5b affords enamine 8, probably via fragmentation of ylide 6b into transient carbene 7b and a subsequent 1,2-hydrogen shift. Transient cyclic C-amino phosphorus ylides 6c and 6d have been prepared by intramolecular addition of a carbanion generated by deprotonation of a phosphorus substituent. Three-membered heterocycle 6c rearranges into alkene 9, whereas the four-membered ring system undergoes a ring opening affording the stable carbene 7d. The latter results pave the route for the synthesis of various mixed carbene-phosphine bidentate ligands.

Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Publishing Authors By Initials

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

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Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Journal Published:

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

Journal: Journal of the American Chemical Society

VOLUME: 128

Page Numbers: 459-64

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 18

MONTH: Jan

YEAR: 2006

Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Keywords Mesh Terms:

KEYWORDS: Phosphines

MESH TERMS: chemistry

Chemical & Substance for Abstract: Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes. Information

Substance Name: Methane

Registry Number: 74-82-8

Grant and Affiliation Information for Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes.

AFFILIATION: UCR-CNRS Joint Research Chemistry Laboratory (UMR 2282), Department of Chemistry, University of California, Riverside, 92521-0403, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: R01 GM068825-01A2

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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