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ADA154608

Publication Date	1983
Personal Author	Burton, D. J.; Cox, D. G.
Page Count	3
Abstract	Flourine-containing phosphoranium salts such as BU3P(+)-CFP(+)Bu3X(-) and PH3P(+)Ph3Br(-) were readily prepared from tertiary phosphines and CFCl3 and CFBr3. In contrast to the normal acylation of phosphonium ylides by acyl halides, Bu3P(+)-CFP(+)Bu3X(-) undergoes a Wittig reaction with F-acyl fluorides to give stereospecifically the trans-vinyl phosphonium salts, Bu3P(+)CF-CFR sub Fx(-) double bond. Alkaline hydrolysis of the phosphonium salt gives the trans-1-hydro-F-olefin. The overall one-pot process provides a novel stereospecific conversion of F-acyl halides to olefins with chain-extention of one carbon. Mechanistically, the process demonstrates that with proper control, the reaction of phosphonium ylides with acyl halides can be diverted to olefination rather than the previously observed acylation sequence.
Keywords	Synthesis(Chemistry) Olefin polymers Acylation Fluorides Hydrolysis Phosphonium compounds Response Salts Sequences Synthesis Reprints Ylides Wittig reactions
Source Agency	Air Force Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	Iowa Univ., Iowa City. Dept. of Chemistry.; Air Force Office of Scientific Research, Bolling AFB, DC.
Supplemental Notes	Pub. in Jnl. of American Chemical Society, v105 p650-651 1983.
Document Type	Journal Article
NTIS Issue Number	198518

Wittig Olefination via Reaction of Fluorine-Containing Phosphoranium Salts and F-Acyl Fluorides. A New Approach to Fluoroolefin Synthesis.

Wittig Olefination via Reaction of Fluorine-Containing Phosphoranium Salts and F-Acyl Fluorides. A New Approach to Fluoroolefin Synthesis.
ADA154608

Publication Date	1983
Personal Author	Burton, D. J.; Cox, D. G.
Page Count	3
Abstract	Flourine-containing phosphoranium salts such as BU3P(+)-CFP(+)Bu3X(-) and PH3P(+)Ph3Br(-) were readily prepared from tertiary phosphines and CFCl3 and CFBr3. In contrast to the normal acylation of phosphonium ylides by acyl halides, Bu3P(+)-CFP(+)Bu3X(-) undergoes a Wittig reaction with F-acyl fluorides to give stereospecifically the trans-vinyl phosphonium salts, Bu3P(+)CF-CFR sub Fx(-) double bond. Alkaline hydrolysis of the phosphonium salt gives the trans-1-hydro-F-olefin. The overall one-pot process provides a novel stereospecific conversion of F-acyl halides to olefins with chain-extention of one carbon. Mechanistically, the process demonstrates that with proper control, the reaction of phosphonium ylides with acyl halides can be diverted to olefination rather than the previously observed acylation sequence.
Keywords	Synthesis(Chemistry) Olefin polymers Acylation Fluorides Hydrolysis Phosphonium compounds Response Salts Sequences Synthesis Reprints Ylides Wittig reactions
Source Agency	Air Force Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	Iowa Univ., Iowa City. Dept. of Chemistry.; Air Force Office of Scientific Research, Bolling AFB, DC.
Supplemental Notes	Pub. in Jnl. of American Chemical Society, v105 p650-651 1983.
Document Type	Journal Article
NTIS Issue Number	198518