Bulletin of the Chemical Society of Japan p. 1690 - 1695 (1985)
Update date:2022-08-17
Topics:
Yamomoto, Gaku
Oki, Michinori
The 400 MHz 1H NMR spectrum of the title compound at -100 deg C in dichloromethane revealed the presence of two isomers in a ratio of 88:12, which results from restricted rotation about the triptycyl-oxygen single bond.The major isomer was assigned to the ap rotamer on the basis of the low temperature 13C NMR spectrum.Dynamic NMR studies gave the activation parameters for the ap<*>+/-sc conversion: ΔH<*> = 11.9+/-0.5 kcal/mol (1 calth = 4.184 J), ΔS<*> = 2.6+/-2.5 eu, ΔG200K<*> = 11.4 kcal/mol.Results of molecular mechanics calculations on the compound are discussed.
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