22780-08-1Relevant academic research and scientific papers
Practical synthesis of gem-difluorides from cyclohexanone: Synthesis of gem-bistrifluoroacetates and their reactions with fluoride nucleophiles
Tojo, Masahiro,Fukuoka, Shinsuke,Tsukube, Hiroshi
, p. 29 - 35 (2010)
Formation of ketone acylals bearing trihaloacetoxy groups and their nucleophilic geminal disubstitution by fluoride ions were investigated. Cyclohexanone reacted with trifluoroacetic anhydride without catalyst to give gem-bistrifluoroacetates via a concerted bimolecular reaction. Treatment with hydrogen fluoride under mild conditions efficiently yielded the corresponding gem-difluorides. In this reaction process, trifluoroacetic acid was recovered and converted to trifluoroacetic anhydride using P2O5. Since gem-difluorides were derived from ketones, HF and P2O5, this constitutes a practical synthesis of gem-difluorides.
