Issue 0, 1983

Polyhalogenoaromatic compounds. Part 50. Reactions of 4-benzyloxytetrahalogenopyridines with nucleophiles

Abstract

Reaction of 4-benzyloxy-3,5-dichloro-2,6-difluoro-(1; R = CH2Ph) and 4-benzyloxytetrachloropyridine (2; R = CH2Ph) with various nucleophiles (N,N-dimethylhydrazine, piperidine, N,N,N′,N′-tetramethylethane-1,2-diamine, triphenylphosphine) occurs unexpectedly at the benzylic methylene group with alkyl–oxygen cleavage to give the corresponding benzylammonium (4) or triphenylphosphonium salt (9) respectively. The molecular structure of the salt derived from 4-benzyloxytetrachloropyridine and N,N-dimethylhydrazine was confirmed by an X-ray study. Preliminary experiments of utilising the benzyl cleavage for the preparation of various benyzl derivatives (PhCH2X;X = CI, Br, I, CN, N3) are described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 2507-2511

Polyhalogenoaromatic compounds. Part 50. Reactions of 4-benzyloxytetrahalogenopyridines with nucleophiles

L. Julia, H. Suschitzky, J. C. Barnes and C. D. S. Tomlin, J. Chem. Soc., Perkin Trans. 1, 1983, 2507 DOI: 10.1039/P19830002507

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