1291074-18-4Relevant academic research and scientific papers
Boron-trihalide-promoted regioselective ring-opening reactions of gem-difluorocyclopropyl ketones
Yang, Tang-Po,Li, Qiang,Lin, Jin-Hong,Xiao, Ji-Chang
, p. 1077 - 1079 (2014/01/17)
Boron trihalide-promoted ring-opening reactions of gem-difluorocyclopropyl ketones to give the corresponding β-trifluoromethyl ketones and β-halodifluoromethyl ketones were described. It was found that boron trihalides act as both Lewis acids and nucleophiles and the proximal bond prefers to cleave in this transformation.
Friedel-Crafts reactions of 2,2-difluorocyclopropanecarbonyl chloride: Unexpected ring-opening chemistry
Dolbier Jr., William R.,Cornett, Eric,Martinez, Henry,Xu, Wei
experimental part, p. 3450 - 3456 (2011/07/06)
The Friedel-Crafts reactions of 2,2-difluorocyclopropanecarbonyl chloride with various arenes did not lead to the straightforward formation of the expected aryl 2,2-difluorocyclopropyl ketones. Instead the reactions proceeded, to various degrees depending on the reactivity of the arene, via an apparent rearrangement of the initially formed acylium ion to form novel aryl 3-chloro-3,3-difluoropropyl ketones. The ring-opened product was formed exclusively, and therefore the reaction may be synthetically useful when relatively unreactive arene substrates such as benzene, toluene, and p-xylene are used. No conditions were found where ring-intact products could be formed exclusively when using substituted benzenes as substrates, with the very reactive substrate thiophene being most selective in that regard, favoring ring intact product 3 with a selectivity of 98:2. The regioselectivity of ring-opening was examined and compared with other related systems computationally.
