Nucleophilic substitutions in five-membered rings. Primary steric effects in thiophen derivatives
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 8,p. 816-819
- https://doi.org/10.1039/p29750000816
Abstract
In order to study primary steric effects (p.s.e.) in nucleophilic substitutions of five-membered rings, the rate of piperidino and benzenethiolate substitution of some 2-L-5-nitrothiophens (Ia—d) and 2-L-3-methyl-5-nitrothiophens (IIa—d) have been measured in methanol. The rate ratios (kH/kMe) obtained show an absence of p.s.e. in piperidino substitutions when the leaving group is halogen but not when L = SO2Ph. Benzenethiolate substitution data show the presence of a large Reinheimer–Bunnett effect.Keywords
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