bp 118–119°C/9 Torr;55–65°C/0.05 Torr;
n25
D 1.4456.
1,2-Bis(t-butyldimethylsilyl)hydrazine is a source of latent hydrazine used in the preparation of stable alkyl
and aryl N-silyl hydrazones, gem-dihalides, vinyl halides, and
room temperature Wolff–Kishner reductions.
Wolff–Kishner Reduction.
A particularly useful reaction of
the N-silyl hydrazones is their use as substrates in the Wolff–
Kishner reaction, where reduction of the corresponding carbonyl
compound can be accomplished at relatively modest temperatures.
This is in marked contrast to the more traditional Wolff–
Kishner reaction, and its Huang–Minlon modification, which
require high temperatures and the use of potassium hydroxide.Room temperature conditions for the Wolff–Kishner reaction,
previously reported by Cram and co-workers, were adapted by
Myers and Furrow to the current N-silyl hydrazone methodology
(eq 4).
