Issue 0, 1974

Aryne chemistry. Part XXXIV. Reactions of NN-dimethylarylamines with tetrahalogenobenzynes

Abstract

Reactions of tetrafluorobenzyne with NN-dimethylarylamines lead to mixtures of products. When the aryne is generated from a Grignard reagent the isolated products are those derived from attack on the arene residue and have been characterised as derivatives of 1,4-dihydro-1,4-ethenonaphthalene and benzocyclo-octene. Two additional products identified in reactions with pentafluorophenyl-lithium are derived from a betaine either by immediate charge neutralisation or by ylide formation followed by a Stevens rearrangement in which aryl migration occurs.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1974, 2688-2693

Aryne chemistry. Part XXXIV. Reactions of NN-dimethylarylamines with tetrahalogenobenzynes

J. P. N. Brewer, H. Heaney, S. V. Ley and T. J. Ward, J. Chem. Soc., Perkin Trans. 1, 1974, 2688 DOI: 10.1039/P19740002688

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