Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol

Xiaofang Wang, Yuxiang Dong, Edward L. Ezell, Jered C. Garrison, James K. Wood, James P. Hagen, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes.

Original languageEnglish (US)
Pages (from-to)2972-2976
Number of pages5
JournalTetrahedron
Volume73
Issue number20
DOIs
StatePublished - Jan 1 2017

Keywords

  • 1,2,6-Trisubstituted adamantanes
  • Polybrominated adamantanes
  • Protoadamantane-adamantane rearrangement
  • Semipinacol rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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