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 language | English (US) |
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Pages (from-to) | 9019-9026 |
Number of pages | 8 |
Journal | Journal of the American Chemical Society |
Volume | 116 |
Issue number | 20 |
DOIs | |
State | Published - Oct 1 1994 |
All Science Journal Classification (ASJC) codes
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry