Issue 0, 1971
From the journal:

Journal of the Chemical Society B: Physical Organic

Amine oxidation. Part IV. The oxidative cyclisation of trialkylamino-alcohols and -amines with alkaline potassium hexacyanoferrate(III)

C. A. Audeh  and  J. R. Lindsay Smith  

Abstract

A selection of trialkylamino-alcohols and -amines have been oxidised to cyclic oxaza- and diaza-compounds by use of aqueous alkaline potassium hexacyanoferrate(III). The oxidation occurs at the trialkylamino-group to give an iminium ion which is converted by the intramolecular nucleophilic addition of the other heteroatom into the cyclic product.

The oxidation of two NN-dimethylphenethylamines gave the monomethyl secondary amines but none of the N-methyl-1,2,3,4-tetrahydroisoquinoline. Clearly cyclisation of the phenethylmethylmethyleneiminium ion does not compete effectively with its solvolysis.

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Article information

DOI
https://doi.org/10.1039/J29710001745
Article type
Paper

J. Chem. Soc. B, 1971, 1745-1747

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Amine oxidation. Part IV. The oxidative cyclisation of trialkylamino-alcohols and -amines with alkaline potassium hexacyanoferrate(III)

C. A. Audeh and J. R. L. Smith, J. Chem. Soc. B, 1971, 1745 DOI: 10.1039/J29710001745

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