2-Bromo-2-nitropropane, reduction

The cathodic reduction of 2-bromo-2-nitropropane in the presence of dimethyl acetylene dicarboxylate leads to 5,5-dimethyl-2,3,4-trimethoxycarbonyl-5-hydropyrrole as the major product (64% yield) (Scheme 85) [125]. 

Aryl-6-nitroanthranils are obtained on heating of 2,4-dinitrobenzaldehydes in sulfuric acid or polyphosphoric acids with aromatic carbohydrates [436-440], Reductive heterocyclization of 2,6-dinitrobenzaldehyde in the presence of 2-bromo-2-nitropropane... 

Involvement of a nitrene seems very likely in sequences where an orf/to-azidoaryl ketone is decomposed thermally producing 3-substituted 2,l-benzisoxazoles. ° In the opposite sense, reduction of ortho-nitm-araldehydes is a very efficient route to 3-unsubstituted 2,1-benzisoxazoles. Both the zinc and the 2-bromo-2-nitropropane are essential components of the reducing mixture. Note the survival of the aromatic halogen in the example shown. ... 

Reductive cyclisation of o-nitrobenzaldehyde with zinc/2-bromo-2-nitropropane in methanol yields 2,1-benzisoxazole 8 <97H(45)235>. The styryl-2,l-benzisoxazoles 10 are formed in... 

Ruegg, U. T. and Rudinger, J., 1977. Reductive cleavage of cystine disulfides with tributylphosphine. Methods in Enzymology 47, 111-116. Shepherd, J. A., Waigh, R. D. and Gilbert, P., 1988. Antibacterial action of 2-bromo-2-nitropropane-l,3-diol (Bronopol). Antimicrob. Agents... 

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