Collect. Czech. Chem. Commun. 1994, 59, 227-230

3,5-Di-tert-butyl-1,2-benzoquinone Cleaves a CC-bond in Vicinal Aminobenzyl Alcohols

Václav Horáka, Yonco Mermerskya and Dalal B. Guirguisb

a Georgetown University, Washington DC., 20057, U.S.A.
b Ein Shams University, Cairo, Egypt


Two vicinal aminobenzyl alcohols, L-threo-1-(4-methylthiophenyl)-2-amino-1,3-propanediol (IIa) and 1-phenyl-2-amino-1,3-propanediol (IIb), underwent, under mild conditions, CC-bond cleavage with 3,5-di-tert-butyl-1,2-benzoquinone (I) producing in high yields 4-methylthiobenzaldehyde (Va) and benzaldehyde (Vb), respectively, and 2-hydroxymethyl-4,6-di-tert-butylbenzoxazole (VII). Ethanolamine (VIII) under identical conditions produced benzoxazole VII. The reported reaction is a second case in which quinone I mimics reactions of pyridoxal.