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

Autor:	Marilyn Wooten, Saadia Faiz, William H. Watson, Mitchell D. Miller, Ted Wiederhold, Joseph K. Agyin, Kurt L. Krause, Benjamin F. Plummer
Rok vydání:	1997
Předmět:	Steric effects chemistry.chemical_classification chemistry.chemical_compound Hydrocarbon chemistry Organic Chemistry Substituent Maleic anhydride Selectivity Medicinal chemistry Aryne Diels–Alder reaction Adduct
Zdroj:	The Journal of Organic Chemistry. 62:9290-9294
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo971610t
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4edc82f6839115937cf2f61d7d9af4df https://doi.org/10.1021/jo971610t Zobrazit plný text záznamu