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• W2012803535 abstract "Highly reactive methanesulfonates (mesylates, ROMs) have been prepared from 1-phenylethanol, cyclohex-2-en-1-ol, diphenylmethanol and p-methoxybenzyl alcohol by treatment with methane-sulfonyl chloride and triethylamine in dichloro- or trichloro-methane at –20 to 0 °C. The mesylates, characterised in solution by 1H and 13C NMR at –20 °C, were obtained in satisfactory purity (ca. 95 %) in cold solutions but they decomposed by reaction with chloride, triethylamine or the parent alcohol. Rate constants for solvolyses in aqueous acetone and aqueous ethanol have been determined by a fast response conductimetric method. Product selectivities for solvolyses of p-methoxybenzyl mesylate in aqueous ethanol and methanol at 0 °C have been determined by HPLC. From additional new or literature kinetic data for solvolyses of corresponding bromides, chlorides and p-nitrobenzoates (OPNB), Br/Cl, OMs/Br and OMs/OPNB rate ratios were calculated; the results are consistent with electronic effects stabilising the carbocationic transition states and increasing OMs/Br rate ratios for these SN1 solvolyses; none of the evidence supports a geminal electronic effect on Br/Cl rate ratios (e.g. caused by stabilisation of the initial state in p-methoxybenzyl chloride). Steric effects on ester/halide rate ratios for solvolyses of tertiary substrates are confirmed. Relative rates over a 1016 range for ester and halide leaving groups are evaluated for solvolyses of 1-phenylethyl substrates in 80 % ethanol–water, updating previous work by Noyce et al. (1972)." @default.
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• W2012803535 date "1994-01-01" @default.
• W2012803535 modified "2023-10-18" @default.
• W2012803535 title "Kinetic and spectroscopic characterisation of highly reactive methanesulfonates. Leaving group effects for solvolyses and comments on geminal electronic effects influencing SN1 reactivity" @default.
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• W2012803535 doi "https://doi.org/10.1039/p29940002531" @default.
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