Aromatic reactivity. Part XLVIII. Hydrogen exchange in the methyl groups of 2-methyl-, 3-methyl-, and 2,3-dimethyl-benzo[b]thiophen

doi:10.1039/J29710002262

Paper

Aromatic reactivity. Part XLVIII. Hydrogen exchange in the methyl groups of 2-methyl-, 3-methyl-, and 2,3-dimethyl-benzo[b]thiophen

Published 1971 · C. Eaborn, G. J. Wright

Journal of The Chemical Society B: Physical Organic

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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.

Study Snapshot

Hydrogen exchange in the methyl groups of 2-methyl-, 3-methyl-, and 2,3-dimethyl-benzo[b]thiophen leads to detritiation in anhydrous trifluoroacetic acid, with rates comparable to those for ring detritiation of [3H]benzen

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Aromatic reactivity. Part XLVIII. Hydrogen exchange in the methyl groups of 2-methyl-, 3-methyl-, and 2,3-dimethyl-benzo[b]thiophen

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References

Citations

Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis.

Amine-mediated electrophilic arene borylation can produce stable MIDA-boronates in moderate to good yields, with various reaction pathways and amine-dependent pathways.

Recent Advances in the Chemistry of Benzo[b]thiophenes

Benzo[b]thiophene chemistry has advanced significantly since 1952, with improved methods for preparing various benzo[b]thiophenes and their applications in various fields.