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When the reaction was carried out with 1 equiv of piperidine and 4 equiv of diisopropylethylamine in the presence of a catalytic amount of TFA in refluxing chloroform, 15% of the desired diamine was obtained
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10. When the reaction was carried out with 1 equiv of piperidine and 4 equiv of diisopropylethylamine in the presence of a catalytic amount of TFA in refluxing chloroform, 15% of the desired diamine was obtained.
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14. This is in fact closely related to similar A2 type hydrolysis of sulfate half esters reported by Kochansky and later by Sharpless, in which either a combination of a mineral or a Lewis acid along with a minimum amount of water can activate the sulfate half ester and assist the nucleophilic attack of nucleophiles (in these cases an ethereal solvent) onto the sulfur atom. See, (a) Goren, M. B.; Kochansky, M. E. J. Org. Chem. 1973, 38, 3510.
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