ChemInform Abstract: Restricted Rotation Involving the Tetrahedral Carbon. Part 61. Syntheses of/and Restricted C(sp3)-C(sp2) Bond Rotation in Triptycenes That Carry C4-Olefinic Substituent at 9-Position.
Abstract
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ChemInform Abstract
The triptycene derivatives (III) and analogues that carry C4-olefinic substituents at the 9-position in which the olefin is connected to C-9 through an sp2 carbon are synthesized from corresponding substituted anthracenes and in situ generated benzyne. The dynamic behaviors of ( III), as observed by dynamic NMR technique, are discussed on the basis of the results of MM2 calculations. The barrier to rotation of the olefinic groups is higher when there is a Me group which directs inside relative to the triptycene skeleton than in the case where no such a Me group exists.
