Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

Benjamin F. Plummer, Saadia Faiz, Ted Wiederhold, Marilyn Wooten, Joseph K. Agyin, Kurt L. Krause, Mitchell D. Miller, William H. Watson

Research output: Contribution to journalArticle

Abstract

The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical π-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride. X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.

Original languageEnglish (US)
Pages (from-to)9290-9294
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number26
DOIs
StatePublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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