Uses
Reagent for:
- Preparation of nitrophenol derivatives and quinones under aprotic reaction conditions
- Conversion of oximes to carbonyl compounds under microwave irradiation
- Catalyst precursor for catalytic gas phase dehydration of acetic acid to ketene
- Crosslinking agent
Application
Bis(tetrabutylammonium) Dichromate (TBADC) is a mild selective oxidizing agent for benzylic and allylic alcohols
[1]. It can oxidize carbon-halogen bonds
[2].
Preparation
Preparative Method of Bis(tetrabutylammonium) Dichromate (TBADC): a concentrated aqueous solution (300 mL) of Potassium Dichromate (29.4 g, 0.1
mol) is added to a saturated aqueous solution (300 mL) of Tetra-n-butylammonium Bromide (64.4 g, 0.2
mol). TBADC precipitates and can be removed by filtration (62.8 g, 90% yield).
reaction suitability
reagent type: oxidant
storage
Bis(tetrabutylammonium) dichromate was reported to be a toxic agent. The reagent should be handled in a fume
hood.
Purification Methods
Wash it with water and dry it in a vacuum. Recrystallise it from hexane (m 79-80o). [Santaniello & Ferraboschi Synth Commun 10 75 1980, Beilstein 4 IV 556.] (Possible CARCINOGEN.)
References
1. (a) Santaniello, E.; Ferraboschi, P. SC 1980, 10, 75. (b) Luzzio, F. A.; Guziec, F. S. OPP 1988, 20, 533.
2. Landini, D.; Rolla, F. CI(L) 1979, 213.
