1,2-BIS-(TERT-BUTYLDIMETHYLSILYL)HYDRAZINE

Chemical Properties

Colourless Oil

Physical properties

bp 118–119°C/9 Torr;55–65°C/0.05 Torr; n25 D 1.4456.

Uses

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).

Preparation

prepared by reacting t-butyldimethylchlorosilane with anhydrous hydrazine at 70??C (eq 1), with or without solvent.

Raw materials

Preparation Products