Cooperative Effect of Carborane and Pyridine in the Reaction of Carboranyl Alcohols with Thionyl Chloride: Halogenation versus Oxidation

被引：23
|
作者：
Terrasson, Vincent [1 ,2 ]
Planas, Jose G. [2 ]
Prim, Damien [1 ]
Vinas, Clara [2 ]
Teixidor, Francesc [2 ]
Light, Mark E. [3 ]
Hursthouse, Michael B. [3 ]
机构：
[1] Univ Versailles St Quentin en Yvelines, CNRS, Inst Lavoisier Versailles, UMR 8180, F-78035 Versailles, France
[2] CSIC, Inst Ciencia Mat Barcelona, Bellaterra 08193, Spain
[3] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1021/jo801672f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thionyl chloride (SOCl2) acts as halogenation reagent in its reaction with 1-[phenyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaborane 1a,b but unexpectedly behaves as an oxidant for 1-[2'-pyridyl(hydroxy)methyl]-2-R-1,2-dicarba-closo-dodecaboranes 2a,b. The synthesis and characterization of all new compounds, including structure determinations of 1a, 2a, 1-[phenyl(chloro)methyl]-2-methyl-1,2-dicarba-closo-dodecaborane 3a, and 1-[2'-pyridyl(oxo)methyl]-2-methyl- 1,2-dicarba-closo-dodecaboranes 4a are reported and the possible pathways are discussed.
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页码：9140 / 9143
页数：4
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