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题名: Chemoselective reduction model of aliphatic esters with sodium borohydride
作者: Lue Xiao-Jie1, 2; Jiang Ju-Xing1, 2; Ren Jie1; Zhu Hua-Jie1
刊名: CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
关键词: aliphatic esters ; chemoselective reduction ; transition state energy ; half-life period ; odd-even carbon effect
英文摘要: 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.
出版日期: 2008-03-10
卷号: 29, 期号:3, 页码:537-541
语种: 英语
收录类别: SCI
学科分类: Chemistry; Multidisciplinary
ISSN号: 0251-0790
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/1889
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Lu, XJ; Jiang, JX; Ren, J; Zhu, HJ.Chemoselective reduction model of aliphatic esters with sodium borohydride,CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE,2008,29(3):537-541
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