Bulletin of the Chemical Society of Japan p. 3023 - 3027 (1983)
Update date:2022-08-11
Topics:
Tanaka
Yamamoto
Oki
1,4-Dimethyl- and 1,2,3,4-tetrahalo-9-(1-methoxyethyl)triptycenes were synthesized by reactions of 9-(1-methoxyethyl)anthracene with appropriate benzynes. Rotamer distributions and rotational barriers about the bridgehead-to-substituent bond were studied by NMR spectroscopy. Rotamer distributions are governed mainly by the steric effect; the major rotamer is assigned to sc*(S*), the minor one to ap, and the third one found only in the tetrafluoro derivative to sc*(R*). *). Rotational barriers are 21-23 kcal mol** minus **1 which are slightly lower than those for the corresponding 9-isopropyltriptycenes.
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