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Dienophile Twisting and Substituent Effects Influence Reaction Rates of Intramolecular Diels−Alder Cycloadditions: A DFT Study

✍ Scribed by Khuong, Kelli S.; Beaudry, Chris M.; Trauner, Dirk; Houk, K. N.

Book ID
120425461
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
129 KB
Volume
127
Category
Article
ISSN
0002-7863

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Comparison of the rates of cyclization of a series of 2-furfuryl methyl fumarates leads to the conclusion that the gem-dimethyl effect is due primarily to higher population of reactive rotamers. Our recent observation of significant rate acceleration of the infmmolecular Diels-Alder reaction of N-f