1,2-联烯基酮的合成与反应

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	1,2-联烯基酮的合成与反应
	李林涛 ; 麻生明
刊名	有机化学
	2000
卷号	20 期号:6 页码:850-860
ISSN号	0253-2786
其他题名	Sythesis and reaction of 1,2-allenyl ketones
通讯作者	麻生明
中文摘要	1,2-联烯基酮可以通过 2- 丙炔基酮异构化反应，　相应有机金属试剂中间体与酯、酰氯或酰胺的反应，[2,3]或[3,3]迁移反应，　Wittig 反应，　消除反应 ,2,3-－联烯醇氧化等方法合成。　由于联烯酮上含有吸电子基团羰基，　它可发生亲核加成、环加成、环化反应。
英文摘要	Recently, much attention has been paid to the chemistry of 1 , 2- allenyl ketones, due to their high and unique reactivity, in this paper we wish to review the synthesis and reaction of 1,2 - allenyl ketones. 1,2 A]lenyl ketones can be synthesized by the following methods: (1) Oxidation of homopmpargylic akohols to the propargyl ketones, followed by the isomerization; (2) Reaction of appropriate organometal]ic reagents with esters, acyl chlorides or amides; (3) Oxidation of 2,3 allenyl alcohols; (4) [2,3] or [3,3] Reanmigenient of the corresponding ftxnctionalized alkynes; (5) Reaction of the corresponding Wittig reagents with acyl chloride or ketenes; (6) Elimination of β - halogen β，γ or α, β－ unsaturated enones; and others. 1 , 2 - Ailenyl ketones can participate nucLeophi]ic addition, cycloaddition and cyclization reactions (1)The l,4 nucleophilic reaction with l,2 allenyl ketones selectively affordedβ，γ or α, β－ unsaturated enonu. Nucleophiles could be ROH, RR'NH, HX. (2) Reaction of LiAH^4, DIBAL or organomagnesium with the carbonyl groups of 1,2--allenyl ketones afforded the 1,2--addition products allenyl alcohols. (3) The cycloaddition of 1,2-allenyl ketones with 1,3-butadienes, 1,3-cyclopentadienes, and furans to provide efficient routes to six-membered heterocyclic componds. (4) 1,2-Allenyl ketones can be themally rearranged to furans. The cyclization reaction can also be catalyzed by silver (I) and Pd(II). (5) Allenyl ketones bearing an aryl group are prone to proceed a new intramolecular electrophilic substitution reaction using BF^3.Oet^2 or Hg(ClO^4)^2 as the catalyst.
学科主题	有机化学
收录类别	SCI
语种	中文
公开日期	2013-01-15
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/11820]
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	李林涛,麻生明. 1,2-联烯基酮的合成与反应[J]. 有机化学,2000,20(6):850-860.
APA	李林涛,&麻生明.(2000).1,2-联烯基酮的合成与反应.有机化学,20(6),850-860.
MLA	李林涛,et al."1,2-联烯基酮的合成与反应".有机化学 20.6(2000):850-860.