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

ydroxy-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 trea tment with water. Reaction of 4 with iodine in aqueous sodium hydroxid e gives a second oxaboracycle, -hydroxy-3-(4-hydroxybenzoyl)-2,1-benzo -xaborolane (5). The X-ray crystal structure determinations of both bo ron heterocycles are reported. Other new compounds reported are -(4-hy droxyphenyl)-2-(1-hydroxyphenyl)-butan-1-one (6), formed by reaction o f 4 with alkaline hydrogen peroxide, and 1-(4-hydroxyphenyl)-2-(2-biph enyl)-butan-1-one (8), formed by coupling of 4 with bromobenzene in th e presence of Pd(PPh(3))(4).