Preparation and Some Subsequent Transformations of Tetraethynylmethane

Ken S. Feldman, Carolyn K. Weinreb, Wiley J. Youngs, John D. Bradshaw

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45 Scopus citations

Abstract

Tetraethynylmethane (1) was synthesized in 10 steps and 33% overall yield from bis[(trimethysilyl)ethynyl] ketone. This route features (1) construction of the critical central quaternary center via the agency of a [3,3] sigmatropic shift and (2) installation of the fourth acetylene unit in a very sterically demanding environment. Alternative routes and model systems which were more informative than productive are also discussed. Finally, transition metal-mediated coupling of the rather unstable 1 (and derivatives) with unsaturated partners furnished a variety of relatively stable polylalkynylated species which could be manipulated without event.

Original languageEnglish (US)
Pages (from-to)9019-9026
Number of pages8
JournalJournal of the American Chemical Society
Volume116
Issue number20
DOIs
StatePublished - Oct 1 1994

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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