Journal of Organic Chemistry p. 1881 - 1889 (1990)
Update date:2022-07-29
Topics:
Yip, Yu Chi
Wang, Xiao-jun
Ng, Dennis K. P.
Mak, Thomas C. W.
Chiang, Ping
Luh, Tien-Yau
W(CO)6-mediated intramolecular desulfurdimerization reactions have been used in the syntheses of bridged 2,2'-disubstituted bifluorenylidenes in satisfactory yields.Ring sizes from 12 to 24 can be synthesized by this reaction.The extension of this reaction for the synthesis of bifluorenylidene-hinged crown ethers is described.The X-ray structure of 6i has been determined.The two fluorenylidene moieties are each planar, making a dihedral angle of 44.9 deg.The first optically active bifluorenylidenes were unequivocally synthesized, and the barriers for the racemization of two such molecules have been determined (12 kcal/mol).The racemization process may arise from the pyramidalization at C9 and/or C9' followed by rapid twisting along the C9-C9' bond.
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