Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 1, Pages 405-407Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801643u
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Funding
- National Science Foundation [CHE-0449740, CHE-0226402, CHE-0521191, CHE-0443647]
- NIH [P20-RR-016464]
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Biphenylation using (Li(THF)(4))(2)center dot Zr(biphe)(3) of hexabromotriptycenes bearing H (1-H) or Bu (1-Bu) at the bridgeheads gave triptycenes with triphenylene blades. The blades extend both perpendicular and parallel to the 3-fold axis and generate a large intramolecular free volume (IMFV) (1-H, AM1, 710 angstrom(3); cf. triptycene, AM1 71 angstrom(3)). Crystals of 1-H Could not be obtained. Triptycene 1-Bu, in which the Bu (groups fill the voids near the bridgehead, was crystalline. X-ray diffraction analysis revealed crystal packing with alternating interlocked corrugated and distorted hexagonal layers.
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