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Zusammenfassung
cf. CA 63: 16236b; 64: 17599f; 65: 9554e. Redn. of PhCH:NBu with activated Al-Hg in alc. gave a .apprx.3:2 mixt. of dimeric PhCH(NHBu)CH(NHBu)Ph (I) and PhCH2NHBu (II). The I-II ratio was explained by the retention time of the Schiff's base on Al surface. The formation of I requires shorter retention time than that of II. The ratio is dependent upon the basicity of the Schiff's base, and higher ...
Zusammenfassung
cf. CA 63: 16236b; 64: 17599f; 65: 9554e. Redn. of PhCH:NBu with activated Al-Hg in alc. gave a .apprx.3:2 mixt. of dimeric PhCH(NHBu)CH(NHBu)Ph (I) and PhCH2NHBu (II). The I-II ratio was explained by the retention time of the Schiff's base on Al surface. The formation of I requires shorter retention time than that of II. The ratio is dependent upon the basicity of the Schiff's base, and higher temp. favors the formation of I without changing the racemic-meso ratio. The redn. of PhCH:NBu-tert gave the dimeric form exclusively. The dimeric product was also favored by the addn. of a Lewis base, e.g. Et3N. A carbonium-immonium ion mechanism for the redn. is discussed.
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