A novel hydride reduction of 2,4,6-tri-τ-butylnitrobenzene

Intramolecular Hydride Transfer Reactions in (Formazanate)Boron Dihydride Complexes

“…We propose that 7b - i is formed by hydride transfer from the BH 2 unit to the ortho -position of mesityl substituent, resulting in its dearomatization to a cyclohexadiene imine. A related dearomatization reaction was reported by Barclay and co-workers in 1973, who showed intermolecular hydride transfer from vitride (NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 ) to 2,4,6-tri- tert -butylnitrobenzene to give 2,4,6-tri- tert -butyl-2,4-cyclohexadienone oxime at room temperature . To the best of our knowledge, the intramolecular hydride shift from a boron hydride to an aromatic ring such as involved in the formation of 7b - i is without precedent in the literature.…”

“…These reactions are promoted by highly reactive multinuclear metal-hydride clusters . The only nontransition metal example we were able to find in the literature is based on an aluminum hydride complex, which was reported by Barclay and co-workers in 1973 . To the best of our knowledge, the transformation from compound 2b to 7b - i is the first example of the dearomatization of an arene by using a molecular boron hydride species.…”