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Reductions with diimide : ウィキペディア英語版 | Reductions with diimide Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide () is oxidized to dinitrogen.〔Pasto, D. J.; Taylor, R. T. ''Org. React.'' 1991, ''40'', 91. 〕 ==Introduction== In 1929, the conversion of oleic acid to stearic acid in the presence of hydrazine was observed.〔Hanuš, J.; Voríšek, J. ''Collect. Czech. Chem. Commun.'' 1929, ''1'', 223.〕 The short-lived intermediate diimide was not implicated in this reductive process until the 1960s. Since that time, several methods of generating transient amounts of diimide have been developed.〔Aylward, F.; Sawistowska, M. ''Chem. Ind. (London)'', 1962, 484.〕〔Cusack, J.; Reese, B.; Risius, C.; Roozpeikar, B. ''Tetrahedron'' 1976, ''32'', 2157.〕 In the presence of unpolarized alkenes, alkynes or allenes, diimide is converted into dinitrogen with reduction (net addition of dihydrogen) of the unsaturated functionality. Diimide formation is the rate-limiting step of the process, and a concerted mechanism involving ''cis''-diimide has been proposed.〔 This reduction represents a metal-free alternative to catalytic hydrogenation reductions, and does not lead to the cleavage of sensitive O–O and N–O bonds. ''(1)''File:DiimideGen.png
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