Rate determination and product studies have disclosed that the fragmentation pattern of radical cations 2-propenyl-1,4-dimethoxybenzene (1+ ·) and 2-propenyl-1,4,5-trimethoxybenzene (2+·) generated in one-electron oxidation of their parent substrates by 4-nitrobenzoyl peroxide (3) in CH3CN is greatly affected by ring-substitution status of the donor molecules. While ringbenzoloxylation (product 5) predominated in the reaction of dimethoxylated substrate (1), the oxidation of trimethoxylated donor 2 ended up with distonic radical cation mediated α,β-di-4-nitrobenzoloxylation as the major pathway.
Research on Chemical Intermediates – Springer Journals
Published: Oct 13, 2004
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