Novel Reduction of 2,6-Di-t-butyl-p-quinols with Sodium Borohydride

Article abstract of DOI:10.1246/cl.1994.961

Reduction of 2,6-di-t-butyl-p-quinols with NaBH4 results unexpectedly in the regio- and stereoselective formation of the corresponding dihydro-p-quinols.The novel reduction occurs via a quinoxyborohydride anion intermediate, which regulates the stereochemistry of the 4- and 6-positions in the products.Aromatization of the products is blocked by the t-butyl groups.