77326-92-2Relevant academic research and scientific papers
A facile preparation method for α,α-difluoroalkanecarboxylic acids and esters. A formal difluoromethylene insertion to alkanecarboxylic acids using radical reaction
Okano, Takashi,Takakura, Nobuyuki,Nakano, Yuko,Okajima, Asako,Eguchi, Shoji
, p. 1903 - 1920 (2007/10/02)
Various alkyl radicals generated by the photoreaction of a series of Barton esters reacted with 1,1-dichloro-2,2-difluoroethene to give radical adducts as the major product accompanied with self-trapping products. Primary, secondary, tertiary, benzyl, and some unsaturated alkyl radicals as well as those with another functional group such as ether, carbonyl, and azide were applicable. Barton esters of diacids also afford 1:2 adducts with a small amount of 1:1 adducts and bis-self-trapping products except for the succinic case. These adducts were hydrolyzed with AgNO3/H2O-THF to α,α-difluoroalkanecarboxylic acids and methanolyzed with AgNO3/MeOH to the corresponding methyl esters. 4-Azido-2,2-difluorobutylic acid and the methyl ester were converted to difluoro-GABA and difluoro-γ-lactams.
α,α-Difluoroalkanecarboxylic acids: A general synthesis via alkyl radical addition to 1,1-dichloro-2,2-difluoroethylene
Okano,Takakura,Nakano,Eguchi
, p. 3491 - 3494 (2007/10/02)
Photodecomposition of alkanoic acid esters of N-hydroxy-2-thiopyridone with 1,1-dichloro-2,2-difluoroethylene gives alkyl-radical-trapped products, which give α,α-difluoroalkanoic acids and their methyl esters on hydrolytic or methanolytic treatment with silver nitrate.
