Abstract
The nitro groups in tertiary or secondary nitro compounds are replaced by hydrogen or deuterium on treatment with tributyltin hydride or deuteride, respectively. This discovery opens a new area in organic synthesis, as a-anions of nitroalkanes can be used as equivalents of alkyl anions. Thus, following new synthetic reactions are devised on the basis of the denitrohydrogenation with Bu3SnH. (1) Conjugate addition of alkyl groups via Michael addition of nitroalkanes followed by denitration. (2) Synthesis of ketones via denitration of α-nitro ketones. (3) Synthesis of alcohols via denitration of β-nitro alcohols. (4) Regioselective deuteration. (5) New substitution reactions via radical substitution and denitration. (6) Regiocontrolled Diels-Alder reactions (7) Radical cyclization of aliphatic nitro compounds. (8) Synthesis of olefins.
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