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ABSTRACT:
SUBMITTER: Levandowski BJ
PROVIDER: S-EPMC6314817 | biostudies-literature | 2018 Mar
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20180307 6
The endo and exo stereoselectivities of Diels-Alder reactions of cyclopropenone, iminocyclopropene, and substituted triafulvenes with butadiene were rationalized using density functional theory calculations. When cyclopropenone is the dienophile, there is a 1.8 kcal/mol preference for the exo cycloaddition with butadiene, while the reaction of 3-difluoromethylene triafulvene with butadiene favors the endo cycloaddition by 2.8 kcal/mol. The influence of charge transfer and secondary orbital inter ...[more]