Issue 8, 1975
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Nucleophilic substitutions in five-membered rings. Primary steric effects in thiophen derivatives

Domenico Spinelli,   Giovanni Consiglio  and  Tommaso Monti  

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.

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Article information

DOI
https://doi.org/10.1039/P29750000816
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1975, 816-819

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Nucleophilic substitutions in five-membered rings. Primary steric effects in thiophen derivatives

D. Spinelli, G. Consiglio and T. Monti, J. Chem. Soc., Perkin Trans. 2, 1975, 816 DOI: 10.1039/P29750000816

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