1-Boraadamantane blows its top, sometimes. The mono-and polyhomologation of 1-boraadamantane

Carl E. Wagner, Kenneth J. Shea

Research output: Contribution to journalArticlepeer-review

38 Scopus citations


(equation presented) 1-Boraadamantane·THF (3) reacts with 1 equiv of dimethylsulfoxonium methylide (4) to afford a monohomologated product. The polyhomologation of 1-boraadamantane·THF by ylide 4 followed by oxidative cleavage generates star polymethylene polymers incorporating a cyclohexane core. However, only one-third of the initiators lead to product formation, resulting in an observed degree of polymerization three times higher than expected. The polyhomologation of 3 was found to contain branch points after the fourth and fifth methylene insertions. At the branch points, the propagating species either terminate in tricyclic trialkylborane cages with collapsed, pyramidal inverted boron centers that are unreactive toward ylide or they continue in uninterrupted polymerization and eventually result in the formation of giant "tube-like" structures such as 5.

Original languageEnglish (US)
Pages (from-to)3063-3066
Number of pages4
JournalOrganic Letters
Issue number20
StatePublished - Oct 4 2001
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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