Chemoselective reduction model of aliphatic esters with sodium borohydride
Lue Xiao-Jie1,2; Jiang Ju-Xing1,2; Ren Jie1; Zhu Hua-Jie1
2008-03-10
发表期刊CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
ISSN0251-0790
卷号29期号:3页码:537-541
摘要Sodium borohydride has been widely used in different organic reductions due to its moderate chemical activity. The reductions of ester with sodium borohydride could produce various alcohols as intermediates for further reactions. The esters with different alkyl substituents are used as the models in sodium borohydride reductions, and on-set temperatures, half-life periods and transition state(TS) energies were obtained experimentally. Some of the TS energetics were computed using B3LYP/6-31 + + G (d, p)//HF/6-31G (d,p) method. The differences of on-set temperatures among these esters were substantial and some observed selectivities were obtained when the aliphatic substituents changed from Me, Et, n-Pr to n-Bu. Odd-even carbon effect, which was first mentioned in our previous report in enantioselective additions of diethylzine to benzaldehyde, was observed again in the reductions. Traditionally, organic theory uses the size of the substitutents to explain the reaction TS energy order. However, the traditional theory can not be used to explain the observed odd-even carbon effect. The reason for this effect happened in different reactions is still unknown. Furthermore, the effect of solvent in the reductions was investigated primarily.
关键词Aliphatic Esters Chemoselective Reduction Transition State Energy Half-life Period Odd-even Carbon Effect
学科领域Chemistry ; Multidisciplinary
收录类别SCI
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:000254265100022
引用统计
被引频次:1[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/1889
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Chinese Acad Sci, Organ Synth & Nat Prod Lab, State Key Lab Phytochem & Plant Resources W China, Kunming Inst Bot, Kunming 650204, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
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Lue Xiao-Jie,Jiang Ju-Xing,Ren Jie,et al. Chemoselective reduction model of aliphatic esters with sodium borohydride[J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,2008,29(3):537-541.
APA Lue Xiao-Jie,Jiang Ju-Xing,Ren Jie,&Zhu Hua-Jie.(2008).Chemoselective reduction model of aliphatic esters with sodium borohydride.CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,29(3),537-541.
MLA Lue Xiao-Jie,et al."Chemoselective reduction model of aliphatic esters with sodium borohydride".CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE 29.3(2008):537-541.
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