Acceleration of a hetero-Diels–Alder reaction by cyclic metalloporphyrin trimers

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Maurus Marty, Zöe Clyde-Watson, Lance J. Twyman, Moshe Nakash and Jeremy K. M. Sanders


Abstract

The hetero-Diels–Alder reaction between a pyridylbutadiene and 3-nitrosopyridine is accelerated by a variety of metalloporphyrin trimers; there is a weak correlation between rate acceleration and product binding strength.


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