Bridgehead functionalization of [1] diadamantane

JJ Sosnowski, AL Rheingold…

Index: Sosnowski, James J.; Rheingold, Arnold L.; Murray, Roger K. Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3788 - 3791

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Citation Number: 11

Abstract

The bromination of [lldiadamantane can be controlled to give selectively 5-bromo-, 5, 5'- dibromo-, or 5, 5', 7, 7'-tetrabromo [lldiadamantane. Refluxing 1-hydroxy [lldiadamantane (8) with bromine and aluminum bromide also provides the tetrabromide. Monitoring the latter reaction shows that 5, 5'-dibromo-and 5, 5', 7-tribromo-[lldiadamantane are intermediates. Treatment of 8 with phosphorus tribromide provides 1-bromo [lldiadamantane which ...