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tert-Butoxybis(dimethylamino)methane

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.

Use as reagent

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(CH3)2)2]+
[CH(N(CH3)2)2]+ + 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

Preparation

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]

References

  1. ^ Kantlehner, Willi; Bowers, Albert (2007). "T-Butoxybis(dimethylamino)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rb350.pub2. ISBN 978-0471936237.
  2. ^ Arnold, Z. (1959). "The preparation of tetramethylformamidinium salts and their vinylogues". Collection of Czechoslovak Chemical Communications. 24 (3): 760–765. doi:10.1135/cccc19590760.