Journal of Organic Chemistry p. 2518 - 2522 (1987)
Update date:2022-08-16
Topics:
McManus, S. P.
Karman, R. M.
Sedaghat-Herati, R.
Neamati-Mazraeh, N.
Hovanes, B. A.
et al.
The lack of scrambling with deuterium-labeled reactants, a nonlinear ethanol-trifluoroethanol plot, and rate acceleration by edded thiourea are used to show that sulfonate esters of methoxyethanol (MeOCH2CH2OH) undergo solvent-assisted displacement in a variety of solvents; neighboring group participation by ether oxygen (RO-3 participation) does not occur.This conclusion is in accord with predictions of rate based on the Taft treatment of substituent effects.On the other hand, the branched derivative MeOCMe2CH2OBs reacts with concerted RO-3 participation to give completely rearranged product.It solvolysis rate is insensitive to added thiourea, the Taft treatment predicts modest anchimeric assistance, and a linear ethanol-trifluoroethanol plot is observed.We discuss the implications of these results relative to the previously observed nonlinear plot for mustard chlorohydrin.
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