Potassium borohydride nitro compounds

Substituted aromatic nitro compounds having a substituent with a positive Hammett sigma constant can be reduced with potassium borohydride to the azoxy stage. 

An interesting reduction of aromatic nitro compounds which uses glucose in an alkaline medium (equation 7) has received little attention. The advantages of this reaction include high yields, rapid rate and ease of product isolation from oxidation by-products. Other reagents which bring about the reduction of nitroanenes to azoxy compounds include potassium borohydride, sodium arsenate, phosphine and yellow phosphorus. Electrolytic methods have also been utilized. ... 

Sodium and potassium borohydrides are above all used for reducing aldehydes and ketones (Sections 3.2.1, 3.2.2) a,p-ethylenic ketones are converted to mixtures [W3]. In alcoholic media or THF, they leave epoxides, esters and lactones, acids, amides, and most nitro compounds unreacted, but they reduce halides (Section 2.1), anhydrides (Section 3.2.6), quartemary pyridinium salts (Section 3.3), double bonds conjugated to two electron-withdrawing groups (Sections 3.2.9, 4.4), and CUPd... 

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