SCHEDULED MAINTENANCE
Polyfluoroalkyl derivatives of nitrogen. Part XL. Reaction of trifluoronitrosomethane with NN-bistrifluoromethylamino-substituted allenes
Abstract
The allenes (CF3)2N·CH:C:CH2and (CF3)2N·CH:C:CH·N(CF3)2 react with trifluoronitrosomethane under mild conditions to give the oxazetidines (CF3)2N·[graphic omitted]CH2 and (CF3)2N·[graphic omitted]CH·N(CF3)2(mixture of two isomers), respectively, as the major products. The oxazetidines decompose quantitatively on flow pyrolysis at 200–250° to give NN-bistrifluoromethylformamide and the iminoethylene CH2:C:N·CF3or (CF3)2N·CH:C:N·CF3. Reaction of the allene (CF3)2N·CH:C:C[N(CF3)2]2 with trifluoronitrosomethane is more complex and a mixture of four 1 : 1 adducts is formed which contains the oxazetidine (CF3)2N·[graphic omitted]:C[N(CF3)2]2, as shown by flow pyrolysis of the mixture to afford NN-bistrifluoromethylformamide and the iminoethylene [(CF3)2N]2-C:C:N·CF3 among the products. The allene [(CF3)2N]2C:C:CH2 does not react with trifluoronitrosomethane under comparable conditions.
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