Tetrafluoro- and tetrachloro-benzyne react with thioanisole to yield 1,2,3,4-tetrahalogeno-5-phenylthiobenzenes (III) in 45 and 61% yield respectively. Labelling experiments show that intramolecular proton transfer occurs to give ylids (II) which break down to give the isolated products.
J. P. N. Brewer, H. Heaney and T. J. Ward, J. Chem. Soc. C, 1969, 355 DOI: 10.1039/J39690000355
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