Journal of the Chemical Society. Perkin transactions II p. 909 - 914 (1984)
Update date:2022-08-28
Topics:
Kevill, Dennis N.
Posselt, Hans S.
Methyl perchlorate reacts with 0.07-0.4 M-methanol in benzene with a kinetic order of ca. 2.3 in methanol.The reaction is accelerated by addition of nitromethane but, in contrast to the corresponding the corresponding methanolysis of triphenylmethyl chloride, decelerated by added phenol.Small concenration of tetra-n-butylammonium perchlorate cause very large increase in the methanolysis rate.The mechanism is essentially SN2 in character but subject to general-base catalysis, either by additional methanol molecules or by perchlorate ion.With phenol present, deactivation of methanol molecules by hydrogen bonding outweight any electrophilic assistance rendered to perchlorate-ion departure.An alternative for the previously studied methanolysis of triphenyl chloride in benzene is presented; unlike previous proposals, this mechanism is compatible with the ratardation of the methanolysis by moderate concentrations of tera-n-butylammonium chloride.
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