Reactions of the nitrosonium ion. 11. Fluoride transfer from complex fluoride anions to carbenium ions in the nitrosative decomposition of aliphatic azides

MP Doyle, JAL Whitefleet, RJ Bosch

文献索引：Doyle,M.P. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 2923 - 2929

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被引用次数: 14

摘要

Results from nitrosative reactions of aliphatic azides, azido nitriles, and phenoxy azides with nitrosonium salts in chloroform are reported. The presence of the basic nitrile or ether functional group causes a significant increase in the yield of fluoroalkane products, from 5% with 1-azidohexane to 50-81% in reactions with azido nitriles. Elimination reactions and protonic decomposition (Curtius rearrangement), which are major competing processes in ...