o-Quinonoid compounds. Part XI. exo-Selectivity in the Diels–Alder reactions of phenyl-substituted o-quinonoid dienes

Autor:	David W. Jones, Richard L. Wife
Rok vydání:	1976
Předmět:	chemistry.chemical_compound chemistry Furan Norbornadiene Organic chemistry Cyclopentene Dimethyl maleate Selectivity Isoprene Derivative (chemistry) Norbornene
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1654-1659
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19760001654
Popis:	Buta-1,3-diene, isoprene, cyclopenta-1,3-diene, dimethyl maleate, norbornadiene, norbornene, cis-but-2-ene, and cyclopentene add to 1,4-diphenyl-2-benzopyran-3-one (2; R1= R2= Ph) to give mostly exo-adducts; only for the addition of furan is the endo-adduct preferred. By comparison with the preferred endo-addition to 2-benzopyran-3-one, its 1-phenyl derivative (2; R1= Ph, R2= H), and 1,3-diphenylinden-2-one (15) the exo-selectivity in additions to (2; R1= R2= Ph) is attributed to inhibition of secondary interactions by non-coplanar phenyl substituents.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d0e6434575e138313689ca9ccc95ec67 https://doi.org/10.1039/p19760001654 Zobrazit plný text záznamu