Evaluation of the enantiomeric resolution of 7,8-dihydroxy-7,8-dihydrobenzo[a]-pyrene and its 6-fluoro and 6-bromo derivatives on polysaccharide-derived stationary phases.

Evaluation of the enantiomeric resolution of 7,8-dihydroxy-7,8-dihydrobenzo[a]-pyrene and its 6-fluoro and 6-bromo derivatives on polysaccharide-derived stationary phases.
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评估 7,8-二羟基-7,8-二氢苯并[a]-芘及其 6-氟和 6-溴衍生物在多糖衍生固定相上的对映体拆分。

DOI:
10.1021/jo020607t
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发表时间:
2003
期刊:
The Journal of organic chemistry.
影响因子:
--
通讯作者:
Lah,Jure
Lah,Jure
中科院分区:
--
文献类型:
--
作者:
Zajc,Barbara;Grahek,Rok;Kocijan,Andrej;Lakshman,MaheshK;Kosmrlj,Janez;Lah,Jure

文献摘要

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用 Daicel Chiralcel CA-I(三醋酸酯纤维素柱)和OG(三氯对甲基苯氨基甲酸酯纤维素柱)分析了苯并[a]芘及其6-氟和6-溴衍生物的(±)-反式-7,8-二氢二醇的对映体拆分和洗脱顺序。为了比较,在OG和柱上对(±)-1,1‘-双-2-萘酚的分离进行了评价。6-halo-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene的(S)-1,1‘-联-2-萘酚和(7S,8S)-异构体与手性吸附剂的相互作用可能相似。
The enantiomeric resolution and the elution order of (±)-trans-7,8-dihydrodiols of benzo[a]pyrene and its 6-fluoro and 6-bromo derivatives were analyzed on three polysaccharide-based columns:  Daicel Chiralcel CA-I (cellulose triacetate), OF, and OG [cellulose tris(4-chloro- and 4-methylphenylcarbamate)]. For comparison, the separation of (±)-1,1‘-bi-2-naphthol was evaluated on the OG and OF columns. Possibly similar interactions of (S)-1,1‘-bi-2-naphthol and (7S,8S)-isomers of 6-halo-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene with the chiral sorbent are suggested.