@article { ISI:000258332500003,
	title = {Bicorannulenyl: Stereochemistry of a C40H18 biaryl composed of two chiral bowls},
	journal = {Journal of Organic Chemistry},
	volume = {73},
	number = {16},
	year = {2008},
	note = {[["fid":"23642","view_mode":"default","type":"media","attributes":"height":"210","width":"500","style":"width: 357px; height: 150px;","alt":"18. bicoannulenyl stereochemistry","title":"18. bicoannulenyl stereochemistry","class":"media-element file-default"]]\&nbsp;\&nbsp; [["fid":23786,"view_mode":"default","type":"media","attributes":"height":"1000","width":"753","style":"width: 226px; height: 300px;","alt":"JOC cover 2008","title":"JOC cover 2008","class":"media-element file-default"]]},
	month = {AUG 15},
	pages = {6073-6078},
	publisher = {AMER CHEMICAL SOC},
	type = {Article},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {The bicorannulenyl molecule is composed of two chiral bowls tethered by a single bond in a helical fashion. This simple combination of two chiral motifs gives rise to rich dynamic stereochemistry, where 12 conformers interconvert through bowl inversions and central bond rotation, and enantiomerizations occur via multistep processes. Interestingly, 8 out of 10 transition states are chiral, giving rise to mostly chiral enantiomerization pathways, where the molecule changes chirality without passing through an achiral conformation. However, analysis of the stereochemical landscape by DFT calculations and variable temperature NMR spectroscopy reveals that the energetically most favorable enantionterization pathway passes through one of the two achiral transition states. Single-crystal X-ray diffraction corroborates the DFT results and provides information on packing modes of bicorannulenyl molecules in the solid state that have not been seen previously for other buckybowls.},
	issn = {0022-3263},
	doi = {10.1021/jo800359z},
	author = {Eisenberg, David and Filatov, Alexander S. and Jackson, Edward A. and Rabinovitz, Mordecai and Petrukhina, Marina A. and Scott, Lawrence T. and Shenhar, Roy}
}
