3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE CLEAVES A CC-BOND IN VICINAL AMINOBENZYL ALCOHOLS

Authors
HORAK V MERMERSKY Y GUIRGUIS DB
Citation
V. Horak et al., 3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE CLEAVES A CC-BOND IN VICINAL AMINOBENZYL ALCOHOLS, Collection of Czechoslovak Chemical Communications, 59(1), 1994, pp. 227-230
Citations number
5
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
59
Issue
1
Year of publication
1994
Pages
227 - 230
Database
ISI
SICI code
0010-0765(1994)59:1<227:3CACIV>2.0.ZU;2-8
Abstract
Two vicinal aminobenzyl alcohols, reo-1-(4-methylthiophenyl)-2-amino-1 ,3-propanediol (IIa) and 1-phenyl-2-amino-1,3-propanediol (IIb), under went, 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-t ert-butylbenzoxazole (VII). Ethanolamine (VIII) under identical condit ions produced benzoxazole VII. The reported reaction is a second case in which quinone I mimics reactions of pyridoxal.