Constructing the OCF2O moiety using BrF3.
A general preparation for aromatic and aliphatic, cyclic as well as linear, symmetric and asymmetric difluoromethylenedioxy derivatives is described. The alcohols were reacted with thiophosgene to give thiocarbonates, which in turn were reacted with BrF3. The fluorination step is complete in seconds with moderate to high yields under mild conditions.
Hagooly
Youlia
Y
School of Chemistry, Tel-Aviv University, Tel-Aviv 69978, Israel.
Rozen
Shlomo
S
D000438:Alcohols / Q000737:chemistry; D017605:Bromine Compounds / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry; D004986:Ether / Q000737:chemistry; D017611:Fluorine Compounds / Q000737:chemistry*; D006839:Hydrocarbons, Acyclic / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D008956:Models, Chemical; D010705:Phosgene / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000438:Alcohols; D017605:Bromine Compounds; D002254:Carbonates; D017611:Fluorine Compounds; D006839:Hydrocarbons, Acyclic; D006844:Hydrocarbons, Cyclic; D006845:Hydrocarbons, Fluorinated; D013438:Sulfhydryl Compounds; C016145:thiophosgene; D004986:Ether; D010705:Phosgene; C507211:bromine trifluoride