Aromatic reactivity. Part XLVIII. Hydrogen exchange in the methyl groups of 2-methyl-, 3-methyl-, and 2,3-dimethyl-benzo[b]thiophen
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 2262-2264
- https://doi.org/10.1039/j29710002262
Abstract
2- and 3-[3H1]Methylbenzo[b]thiophen and [2-Me-3H1]-2,3-dimethylbenzo[b]thiophen undergo detritiation in anhydrous trifluoroacetic acid, the first-order rate constants at 70° being 14·1 × 10–7, 2·6 × 10–7, and 1·1 × 10–7 s–1, respectively. The rate for the least reactive compound is comparable to that for ring detritiation of [3H]benzene. The results are interpreted in terms of a mechanism involving reversible attachment of a proton to the ring carbon atom ortho to the [3H]methyl group, followed by loss of a proton from the latter to give an olefinic species.Keywords
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