Thiophilic ring opening reactions of 3,3-bis(trifluoromethyl)-5-alkoxy-1,2-dithiolanes under action of nucleophiles

Add time:08/03/2019    Source:sciencedirect.com

The reaction of 3,3-bis(trifluoromethyl)-5-alkoxy-1,2-dithiolanes (RO= OEt or OBu-n) proceeds through thiophilic attack of BuLi leading to the formation of ring-opened product BuSCH(OR)CH2C(CF3)2SLi, which can be converted into the corresponding thiols or sulfides by the reaction with H+ or alkyl halide. Interaction of 3,3-bis(trifluoromethyl)-5-n-butoxy-1,2-dithiolane with CF3Si(CH3)3 resulted in unusual reaction leading to the formation of CF3SCH(OBu)CH2C(CF3)=CF2 (7). The treatment of 7 with CsF in the presence pentafluoropyridine led to equimolar mixture of 2-n-butoxy-1,1-bis(trifluoromethyl)cyclopropane and 4-(trifluoromethylthio)tetrafluoropyridine (as a result of interception of liberated in this process CF3S- anion by pentafluoropyridine).

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