104501-79-3Relevant articles and documents
Nucleophilic difluoromethylation of epoxides with PhSO(NTBS)CF2H by a preorganization strategy
Shen, Xiao,Liu, Qinghe,Luo, Tao,Hu, Jinbo
, p. 6795 - 6800 (2014/06/09)
Unlike the facile synthesis of β-monofluoromethyl alcohols by nucleophilic monofluoromethylation of epoxides, the synthesis of β-difluoromethyl alcohols by nucleophilic difluoromethylation of epoxides still remains a challenge. Herein, studies on tackling this problem with PhSO(NTBS)CF2H (2; TBS=tert-butyldimethylsilyl) are reported. The preorganization of 2 and epoxides with BF3Et2O was found to be crucial for the reaction. The reaction shows excellent regioselectivity and has a broad substrate scope. The facile transformation of the ring-opened products to β-difluoromethyl, γ-difluoromethyl, and β-difluoromethylenyl alcohols demonstrates the synthetic utility of the reaction.
SYNTHESES OF β,β-DIFLUOROCARBOXYLIC ACID DERIVATIVES THROUGH THE CLAISEN REARRANGEMENT OF 1,1-DIFLUORO-1-ALKEN-3-OLS
Taguchi, Takeo,Morikawa, Tsutomu,Kitagawa, Osamu,Mishima, Takashi,Kobayashi, Yoshiro
, p. 5137 - 5140 (2007/10/02)
3,3-Difluoro-4-alkenoic esters (3) were obtained through the Claisen rearrangement of 1,1-difluoro-1-alken-3-ols (1) with ortho ester.Keywords-Claisen rearrangement; 1,1-difluoroethene; dibromodifluoromethane; trimethyl orthoacetate