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- Title
Substituent Effects in the Nitrobenzene and Copper (II) Oxidations of Some Hydroxystilbene Lignin Model Compounds.
- Authors
Dershem, Stephen M.; Fisher, Thomas H.; Johnson, Sara; Schultz, Tor P.
- Abstract
The nitrobenzene and copper (II) oxidations of 4-hydroxystilbenes 2 gave moderate yields of p-hydroxybenzaldehyde. No aldehyde was obtained in the absence of water. A Hammett substituent effect study found a ρ value of - 0.48 versus o+ for both the copper (II) and nitrobenzene oxidations. These results are consistent with a homolytic mechanism involving the benzylic hydroxyl groups of intermediate alcohols 1. A polar transition state in the rate-controlling cleavage of benzyl radicals is postulated to explain the o+ dependence.
- Publication
Holzforschung: International Journal of the Biology, Chemistry, Physics, & Technology of Wood, 1988, Vol 42, Issue 3, p163
- ISSN
0018-3830
- Publication type
Article