Tetrahedron p. 2117 - 2122 (1984)
Update date:2022-07-30
Topics:
Laureillard, J.
Casadevall, E.
Solvolysis rates in methanol and 97percent hexafluoroisopropanol (HFIP) for four β-methyl and β-phenyl bicyclic tosylates, show that solvent nucleophilic assistance is operating in the former solvent.However, in 97percent HFIP, for three of the mentioned compounds, the mechanism involves ? or ? neighboring group assistance.The factors influencing the occurrence of these processes are discussed.Owing to these possible neighbouring group assistances in non-nucleophilic solvents used to obtain kc reference mechanisms, it is concluded that the ks/kc ratio which was proposed as a quantitative evaluation of solvent nucleophilic assistance must be used with caution.
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