Synthesis of Tetraalkenylmethane: Building Blocks for Three-Dimensional Hydrocarbon Networks

Abstract

In this paper, we show a common strategy to synthesize tetraalkenylmethanes, a cross-linker series for building three-dimensional hydrocarbon networks. To demonstrate the feasibility of this method, we have synthesized tetrapentenylmethane. Attempts to synthesize this cross-linker from pentaerythrityl tetrabromide using substitution reactions resulted in the formation of a spiro compound due to intramolecular cyclization. We also show that the difficulty in reactions at the neopentyl carbon site is due to the neopentyl carbanion stability, not the sterics.

Keywords:

• Monomer
• tetrafunctional cross-linkers
• neopentyl carbon
• carbanion stability
• and sterics

Acknowledgments

We thank National Institute of Aerospace for financial support. We also thank Dr. Matthew Herzog at the NASA Langley Research Center for fruitful discussions.