2-Alkyl-1,3-dithiane derivatives, easily made from alkyl bromides and the parent 1,3-dithiane, were reacted with BrF 3 to form the corresponding 1,1-difluoromethyl alkanes (RCHF 2 ) in 60−75% yield. The reaction proceeds well with primary alkyl halides. The limiting step for secondary alkyl halides is the relatively low yield of the dithiane preparation. The two sulfur atoms of the dithiane are essential for the reaction.
[reaction: see text]. Various alkyl and aryl azides, readily obtained from halides or alcohols, were transformed into the corresponding nitriles using bromine trifluoride in moderate to good yields. The reaction is general and gives positive results with aliphatic, aromatic, cyclic, and functionalized azides. It can also be applied to the synthesis of optically active nitriles.
Both alkyl and aryl chlorothioformates could readily be obtained from the corresponding alcohols and thiophosgene. These families of compounds were treated with BrF 3 to form the corresponding alkyl and aryl chlorodifluoromethyl ethers in 60-85 % yields. The method is suitable for constructing
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