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48.1.3.4.5.1 Variation 1: Free-Radical Denitration Reactions

DOI: 10.1055/sos-SD-048-00127

Drabowicz, J.; Krasowska, D.; Wicha, J.Science of Synthesis, (200948258.

A tertiary or secondary nitro group in compounds 29 bearing electron-withdrawing substituents can be replaced by hydrogen (or deuterium) in good yields on treatment with 1.2 equivalents of tributyltin hydride (or deuteride) in refluxing benzene in the presence of 2,2-azobisisobutyronitrile (0.1 equiv) to give alkanes 30 (Scheme 22).[‌112‌‌114‌] Functionalities such as ketone, ester, cyano, and chloro groups are tolerated. Higher temperature and a large excess of tributyltin hydride enables the denitration of nonactivated secondary nitro groups.[‌115‌] Primary nitro groups are usually not affected.

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