Restricted rotation involving the tetrahedral carbon. XXXV. Stereodynamics of 9-(3, 5-dimethylbenzyl) triptycene derivatives.
G Yamamoto, M Oki
Index: Yamamoto, Gaku; Oki, Michinori Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 2 p. 473 - 480
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Citation Number: 31
Abstract
Stereodynamics of a variety of 9-(3, 5-dimethylbenzyl) triptycene derivatives was studied. Atropisomerism about the bridgehead-to-methylene bond was realized in a triply peri- substituted derivative, 8, 13-dichloro-1, 4-dimethyl-9-(3, 5-dimethylbenzy) triptycene: the activation enthalpy for the ap→±sc conversion was 26.4 kcal/mol. Barriers to rotation about the bridgehead-to-methylene bond in a variety of triply, doubly, and singly peri-substituted ...
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