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Strain-induced mechanism change: the limit of strain tolerance in intramolecular nucleophilic substitution?

JM Charles

文献索引:Jeffery, Stephen M.; Niedoba, Stefan; Stirling, Charles J. M. Journal of the Chemical Society, Chemical Communications, 1992 , # 8 p. 650 - 652

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被引用次数: 6

摘要

The effect of strain on reactivity has been subjected to much recent examination and a body of quantitative data bearing on this matter is now available.' In the case of intramolecular nucleophilic substitution by carbanions [eqn. (l)] it has been found2 that the enthalpies of activation for cyclisation are insensitive to the excess enthalpy'll-3 of the ring system being formed, at least in the region spanning 0-113 kJ mol-1. Gaoni4 has shown, however, that the inherent strain of a cyclic ...