Hydrohalogenation reaction of substituted 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides | |
Ma SM(麻生明) ; Xie HX(谢贺新) ; Wang GW(王光伟) ; Zhang JL(张建良) ; Shi ZJ(施章杰) | |
刊名 | Synthesis
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2001 | |
期号 | 5页码:713-730 |
ISSN号 | 0039-7881 |
其他题名 | 1,2联烯羰酸、酯、酰胺、腈、二芳基氧化磷的氢卤化反应 |
通讯作者 | 麻生明 |
英文摘要 | The hydrohalogenation reaction of 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides with HX or MX(X=I,Br, Cl,M=Na, Li) in different solvents, such as HOAc, CF^3CO^2H, and CF^3CO^2H-HOAc(1:1) was studied. The reaction is a nucleophilic conjugate addition in nature and provides efficient entries to 3-halo-3-enoic acids, esters, amides, nitriles, and 2-haloallyl diphenyl phosphine oxides. The β,γ-over α,β-selectivity and stereoselectivity depend on the solvent (s) and the temperature applied. In most cases, the Z-and E-isomers can be easily separated by chromatography on silica gel. The subsequent cross-coupling reaction with organometallic reagents and terminal alkynes showed the synthetic potential of these products. |
学科主题 | 金属有机化学 |
收录类别 | SCI |
原文出处 | http://dx.doi.org/10.1055/s-2001-12759 |
语种 | 英语 |
WOS记录号 | WOS:000168345600009 |
公开日期 | 2013-01-15 |
内容类型 | 期刊论文 |
源URL | [http://202.127.28.38/handle/331003/11830] ![]() |
专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
推荐引用方式 GB/T 7714 | Ma SM,Xie HX,Wang GW,et al. Hydrohalogenation reaction of substituted 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides[J]. Synthesis,2001(5):713-730. |
APA | 麻生明,谢贺新,王光伟,张建良,&施章杰.(2001).Hydrohalogenation reaction of substituted 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides.Synthesis(5),713-730. |
MLA | 麻生明,et al."Hydrohalogenation reaction of substituted 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides".Synthesis .5(2001):713-730. |
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