Bis(trimethylsilyl) sulfide (TMS2S) is used
to reduce aromatic nitro groups to amines and the oxides of sulfur,
selenium, and tellurium. Conditions for nitro group reduction
(eq 1) are forcing; however, yields are good. Reactions of TMS2S
with primary aliphatic nitro groups result in the formation of
the thiohydroxamic acids (eq 2) which can be isolated or carried
further to the nitrile. Secondary alkyl nitro derivatives provide oximes. Sulfoxides are reduced to sulfides, selenoxides to selenides,
and telluroxides to tellurides. Conditions are mild and
work well on both the aliphatic and aromatic oxides.
