Role of addition compounds in the halogenation of benzofurans and benzothiophens
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 266-271
- https://doi.org/10.1039/p29760000266
Abstract
The bromination of benzofuran and its 2-methyl, 3-methyl, and 2, 3-dimethyl derivatives and the chlorination of 2, 3-dimethylbenzothiophen were investigated in CS2 at –40 and –50° by n.m.r. spectroscopy. In all cases the formation of an adduct between the halogen and the heteroaromatic derivative is observed. Decomposition of the adduct leads to ring halogenated products with benzofuran and the monomethylbenzofurans, and to side-chain halogenated compounds with the 2, 3-dimethyl derivatives. These results are discussed in terms of mechanism of both conventional and non-conventional electrophilic aromatic substitution.Keywords
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