硫醇催化的(S)-N,N-二甲基-1-二茂铁基乙胺的外消旋化

Racemization of (S)-N,N-dimethyl-1-ferrocenylethylamine with the Catalyst of Thiol

摘要:

以硫醇为催化剂，偶氮二异丁腈（AIBN）为引发剂，经自由基反应，使(S)-N,N-二甲基-1-二茂铁基乙胺发生外消旋化。通过实验考察了各反应条件对外消旋化效果的影响，结果表明，在以反应物摩尔比为n((S)-N,N-二甲基-1-二茂铁基乙胺):n(苄硫醇):n(AIBN)= 1:1.2:0.6，AIBN的滴加时间为18h，甲苯为溶剂，回流条件下反应时，(S)-N,N-二甲基-1-二茂铁基乙胺能够完全外消旋化。此外，合成得到了含巯基的聚苯乙烯交联树脂催化剂，并初步考察了该催化剂的催化效果，外消旋化合物的e.e.%可至12%。

Abstract:

The enantiomerically pure (S)-N,N-dimethyl-1-ferrocenylethylamine was racemized by a free radical process, with the catalyst of thiol and the initiator of azodiisobutyronitrile (AIBN). The effect of reaction conditions on racemization was optimized by experiments. The results showed that (S)-N,N-dimethyl-1-ferrocenylethylamine could be completely racemized under the following reaction conditions: the molar ratio of (S)-N,N-dimethyl-1-ferrocenylethylamine to thiol and AIBN was 1:1.2:0.6, AIBN was added dropwise in 18 h, and the reaction mixture was refluxed in toluene. Besides, the catalyst of a novel crosslinked mercaptopolystyrene resin was synthetized, and the e.e.% of the racemate could be reduced to 12% with tentative research on the catalytic effect.