Abstract
NN-Dimethylbenzylamine has been oxidatively demethylated to N-methylbenzylamine and debenzylated to benzaldehyde by iodosylbenzene and by t-butyl hydroperoxide catalysed by tetraphenylporphyrinato-iron(III) or -manganese(III) chloride. The influence of substituents on the aromatic ring and of deuteriation of the benzylic hydrogens on the relative reactivity of the substrates and on the product distribution has been studied. The results suggest that the initial step in the metalloporphyrin-catalysed iodosylbenzene oxidations is an electron-transfer from the amine to a high valent oxometal species, whereas, with t-butyl hydroperoxide the mechanism is one of hydrogen abstraction from the amine by the t-butoxyl radical. The mechanisms of the subsequent steps are discussed.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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