ORTHO-DIRECTED ELECTROPHILIC BORONATION OF A BENZYL KETONE - THE PREPARATION, X-RAY CRYSTAL-STRUCTURE, AND SOME REACTIONS OF 4-ETHYL-1-HYDROXY-3-(4-HYDROXYPHENYL)-2-OXA-1-BORANAPHTBALENE

被引：39

作者：

ARCUS, VL ^{[1
]}

MAIN, L ^{[1
]}

NICHOLSON, BK ^{[1
]}

机构：

[1] UNIV WAIKATO,DEPT CHEM,HAMILTON,NEW ZEALAND

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1993年 / 460卷 / 02期

关键词：

D O I：

10.1016/0022-328X(93)83139-M

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

4-Ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene (4) is formed in 78% yield from the reaction of 1-(4-metho-xyphenyl)-2-phenylbutan-1-one with an of excess boron tribromide in dichloromethane followed by treatment with water. Reaction of 4 with iodine in aqueous sodium hydroxide gives a second oxaboracycle, 3-ethyl-1-hydroxy-3-(4-hydroxybenzoyl)-2,1-benzo-xaborolane (5). The X-ray crystal structure determinations of both boron heterocycles are reported. Other new compounds reported are 1-(4-hydroxyphenyl)-2-(1-hydroxyphenyl)-butan-1-one (6), formed by reaction of 4 with alkaline hydrogen peroxide, and 1-(4-hydroxyphenyl)-2-(2-biphenyl)-butan-1-one (8), formed by coupling of 4 with bromobenzene in the presence of Pd(PPh(3))(4).

引用

页码：139 / 147

页数：9

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