Self-activated supramolecular reactions: Effects of host-guest recognition on the kinetics of the Diels-Alder reaction of open-chain oligoether quinones with …

A Tsuda, C Fukumoto, T Oshima

Index: Tsuda, Akihiko; Fukumoto, Chikako; Oshima, Takumi Journal of the American Chemical Society, 2003 , vol. 125, # 19 p. 5811 - 5822

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Citation Number: 23

Abstract

Diels-Alder reactions of acyclic oligoether-substituted quinones 1b, 1c, 2b, and 2c with cyclopentadiene were accelerated by the addition of alkali and alkaline earth metal perchlorates, and scandium trifluoromethane sulfonate (kc/kf= 1.2-23 for univalent cations, 11-1160 for divalent cations, and 1700-192 000 for Sc3+, where kc and kf are the rate constants for the metal complexed and uncomplexed quinones, respectively). The shorter- ...