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Cyto toxic compounds part 23 reactions of the methanesulfonates of 2 n aryl n methylamino propan 1 ols and of 1 n aryl n methylamino propan 2 ols with nucleophiles



Cyto toxic compounds part 23 reactions of the methanesulfonates of 2 n aryl n methylamino propan 1 ols and of 1 n aryl n methylamino propan 2 ols with nucleophiles



Journal of the Chemical Society Perkin Transactions I (4): 943-949



Syntheses of the primary alcohols p-RC6H4.cntdot.NMe.cntdot.CHMe.cntdot.CH2.cntdot.OH (from ethyl 2-bromopropanoate) and of the secondary isomers p-RC6H4.cntdot.NMe.cntdot.CH2.cntdot.CHMe.cntdot.OH (from propylene oxide) are described (R = H, Cl, OMe, or NO2). In solution, the primary methanesulfonates rearrange to the secondary isomers, a process facilitated by an electron-donating aryl substituent. Reactions of the primary and the secondary methanesulfonates with methanol, sodium methoxide, acetic acid, potassium acetate, tetramethylammonium acetate, sodium phenyl sulfide, sodium benzyl sulfide, lithium bromide and sodium azide show that with weak nucleophiles the intermediate aziridinium ion is opened almost exclusively to give the secondary substitution product: with more powerful nucleophiles some sterically-controlled opening occurs to give also some primary product. When the formation of the aziridinium ion is retarded by the presence of an electron-attracting aryl substituent, strong nucleophiles can effect direct SN2 substitution on the methanesulfonates to give unrearranged products. The N-methyl resonances in the 1H NMR spectra of the primary compounds are consistently at higher field than those of the secondary isomers.

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