η-(2-乙氧基乙烯基乙烯酮)铁(0)配合物与1-卤代炔烃环加成反应生成的卤代邻苯二酚。
Halogenated catechols from cycloaddition reactions of η-(2-ethoxyvinylketene)iron(0) complexes with 1-haloalkynes.
作者信息
Truong Jimmy, Caze Vioela, Akhani Ravish K, Joshi Gayatribahen K, Kakalis Lazaros, Matsunaga Nikita, Schnatter Wayne F K
机构信息
Long Island University, Department of Chemistry and Biochemistry, 1 University Plaza, Brooklyn, New York 11201, USA.
出版信息
Tetrahedron Lett. 2010 Feb 10;51(6):921-923. doi: 10.1016/j.tetlet.2009.12.029.
Abstract
1-chloroalkynes and 1-bromohexyne undergo cycloaddition reactions with ethoxyvinylketeneiron(0) complexes to form chloro and bromocatechols. With most substituents, the halogen is incorporated ortho to the phenolic hydroxyl group regioselectively. With chloroethyne, chlorohexyne, and methyl chloropropiolate, the reverse regioselection is observed. Ab initio calculations reveal that the products are, in most cases, nearly isoenergetic, which indicates that the intermediate ketene-alkyne adduct geometry must be important in determining the product distribution.
摘要
1-氯炔烃和1-溴己炔与乙氧基乙烯基乙烯酮铁（0）配合物发生环加成反应，形成氯代和溴代儿茶酚。对于大多数取代基，卤素选择性地在位酚羟基的邻位引入。对于氯乙炔、氯己炔和丙炔酸甲酯，则观察到相反的区域选择性。从头算计算表明，在大多数情况下，产物的能量几乎相等，这表明烯酮-炔烃加合物中间体的几何结构在决定产物分布方面一定很重要。
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本文引用的文献
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