tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.
Also known as Bredereck's reagent, it is used for formylation (introduction of the CHO group).[1] Protonation releases tert-butyl alcohol, giving tetramethylformamidinium, which displaces active C-H bonds:
(CH3)3COCH(N(CH3)2)2 + H+ → (CH3)3COH + [CH(N(CH<sub>3</sub>)<sub>2</sub>)<sub>2</sub>]+
[CH(N(CH<sub>3</sub>)<sub>2</sub>)<sub>2</sub>]+ + CH2Z2 → Z2CHCH(N(CH3)2)2 + H+ The resulting bis(dimethylamino)methyl derivative in turn releases dimethylamine to give an enamine, which hydrolyzes.
Z2CHCH(N(CH3)2)2 → Z2C=CHN(CH3)2 + HN(CH3)2
Z2C=CHN(CH3)2 + H2O → Z2CHCHO + HN(CH3)2
Tert-Butoxybis(dimethylamino)methane is obtained from tetramethylformamidinium chloride by reaction with tert-butoxide. Tetramethylformamidinium salts are obtained by the reaction of dimethylformamide (DMF) with dimethylcarbamoyl chloride[2]