Bulletin of the Chemical Society of Japan p. 2977 - 2980 (1980)
Update date:2022-07-31
Topics:
Nakamura, Mikio
Oki, Michinori
A series of 10,10-disubstituted 9-(2,6-xylyl)-9,10-dihydroanthracene derivatives have been prepared and their conformations and barriers to internal rotation about the Cxylyl-C9 bond have been examined.These compounds exist predominantly as a pseudo-equatorial form in the ground state for rotation.A large effect is inserted by the substituents in 10 position on barriers to rotation and is interpreted in terms of a rotation-inversion mechanism rather than a simple rotation mechanism for the methyl-exchange process which is observed by 1H NMR spectra.The highestbarrier to rotation has been found in the compound having two peri-chloro groups and a hydroxyl group in 9-position.The high barrier is ascribed to destabilization of the transition state, where 9-aryl group takes axial conformation, due to the three electronegative groups which are forced to be arranged parallelly in quite a near region.The change of 9-OH to 9-H thus decreases the barrier to rotation when peri-chlorines are present, while the increase in barrier is observed as in the case of 9-aryfluorenes and 9-arylxanthenes when they are absent.
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