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

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Title:3,5-Di-tert-butyl-1,2-benzoquinone Cleaves a CC-bond in Vicinal Aminobenzyl Alcohols
Creators:
Horák, Václav
Mermersky, Yonco
Guirguis, Dalal B.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 1, pp. 227-230

Abstract

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

Title:3,5-Di-tert-butyl-1,2-benzoquinone Cleaves a CC-bond in Vicinal Aminobenzyl Alcohols
Creators:
Horák, Václav
Mermersky, Yonco
Guirguis, Dalal B.
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:1
Page Range:pp. 227-230
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19940227UNSPECIFIED
ID Code:435
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:01

Citation

Horák, Václav; Mermersky, Yonco; Guirguis, Dalal B. (1994) 3,5-Di-tert-butyl-1,2-benzoquinone Cleaves a CC-bond in Vicinal Aminobenzyl Alcohols. Collection of Czechoslovak Chemical Communications, 59 (1). pp. 227-230. ISSN 0010-0765

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