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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 11, Number 2
BKCSDE 11(2)
February 20, 1990 

 
Title
Dioxygen Transfer from 4a-Hydroperoxyflavin Anion to Isomeric Aminophenolates
Author
Sam Rok Keum*, Ki Bong Lee, Thomas C. Bruice
Keywords
Abstract
The dioxygen transfer reaction from N5-ethyl-4a-hydroperoxy-3-methyllumiflavin anion (4a-FlEtOO-) has been extended to isomeric aminophenol systems (1a-4a). O-aminophenol (o-AP, 1a & 2a) and p-aminophenol(p-AP, 3a & 4a) were turned out to be good substrates, whereas m-aminophenol(m-AP, 5a) was not. This is due to the charge location which is not on the carbon bearing the amino group. o-AO's react with 4a-FlEtOO- to give isophenoxazine derivatives (6 & 7) and with p-AP's to produce p-benzoquinone derivatives (8 & 9). The partition coefficients (k2/k3) of 1a & 2a were 4.84×l0-4 & 1.66×l0-5 M, respectively and those of methylated aminophenolates, 2a & 4a were 4-10 times greater than nonmethylated substrates, 1a & 3a
Page
95 - 99
Full Text
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