Study Of Unsaturated Fluoro-building Block

In Chapter I, the corresponding monofluorinated cycloadducts were synthesized in moderate yields by the 1,3-dipolar cycloaddition reactions between 2,2-difluorovinyl tosylate and N-phenacyl pyridinium or isoquinolinium, N-cyanomethylene pyridinium or isoquinolinium, N-ethoxycarbonylmethylene pyridinium or isoquinolinium ylides and benzimidazolinium N-ylides in the presence of base. When the same N-ylides were allowed to react with 2,3,3-trifluoro-1-propenyl tosylate, the unexpected products formylated indolizines and their derivatives were obtained.In Chapter II, reactions of O- and S-containing nucleophiles with 2,2-difluorovinyl tosylate were studied. It is found that the O- and S-nucleophiles attacked to the terminal CF2 carbon of 2,2-difluorovinyl tosylate regiospecifically at room temperature, affording α,α-difluoromethylene ethers or thio-ethers in moderate to good yields.In Chapter III, Fluoroalkylated triazo-compounds (RFCH2N3) were synthesized from fluoroalkylated alcohols (RFCH2OH), which were synthesized from fluoroalkylated iodides (RFI). For the next step, the fluoroalkylated triazo-compounds (RFCH2N3) reacted with triphenylphosphine affording fluoro phosphorous imines, N-Wittig reagents. The reactions of these reagents with CO2 and CS2 were studied.