Hydrohalogenation reaction of substituted 1,2-allenic carboxylic acids, esters, amides, nitriles, and diphenyl phosphine oxides

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	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
	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.