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A Combined computational-experimental study of the kinetics of intramolecular Diels - Alder reactions in a series of 1,3,8-nonatrienes

Lording, William J; Payne, Alan D; Cayzer, Tory N; Paddon-Row, Michael; Sherburn, Michael


Activation enthalpies for a series of five 1,3,8-nonatriene intramolecular Diels–Alder (IMDA) reactions involving substrates 1–5 have been determined experimentally and Singleton’s natural abundance method has been employed to determine kinetic isotope effects in the IMDA reaction of fumarate 3. The activation enthalpies for the IMDA reactions of the systems possessing a –CH₂OCH₂– diene/dienophile tether are significantly smaller than their counterparts possessing the –CH₂OC(=O)– tether. The...[Show more]

CollectionsANU Research Publications
Date published: 2014-10-14
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH14430


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