PHOTOCHEMICAL-SYNTHESIS OF C-14-LABELED DIBENZ[A,H]ANTHRACENE

被引:11
作者
PLATT, KL
SETIABUDI, F
机构
[1] Institute of Toxicology, University of Mainz
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 15期
关键词
D O I
10.1039/p19920002005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carrier-free (5,12-C-14]dibenz[a,h]anthracene (DBA, 12*) has been prepared for the first time using [C-14]methyl iodide as the source of the label. The key step in this radiosynthesis consisted of the regiospecific photocyclization of 2',5'-divinyl-1,1':4',1''-terphenyl 10* to 5,6,12,13-tetrahydro-DBA 11* followed by dehydrogenation to 12* with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone). Divinylterphenyl 10* was obtained from 2',5'-bis(bromomethyl)-1,1':4',1''-terphenyl 3 via the diformyl derivative 9 and its Wittig olefination with the triphenylphosphonium salt of (CH3I)-C-14. Thus 12* was synthesized with a radiochemical purity exceeding 99%. The chemical yield amounted to 58% from 9 in the case of 12* with a specific activity of 391 MBq mmol-1 and to 12% in the case of carrier-free 12* with a specific activity of 4.14 GBq mmol-1. Wide applicability of this radiosynthetic approach to the preparation of many other carbon-14 labelled polycyclic aromatic hydrocarbons can be envisaged.
引用
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页码:2005 / 2009
页数:5
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