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Digitale Medien

Diastereoselective Intramolecular meta Photocycloaddition of Side-Chain-Substituted 5-(2-Methoxyphenyl)pent-1-enes (1999)

Timmermans, Johan L. ; Wamelink, Marc P. ; Lodder, Gerrit ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 463-470

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Details

ISSN: 1434-193X

Schlagwort(e): meta Photocycloaddition ; Photochemistry ; Steric hindrance ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.

Zusätzliches Material: 3 Tab.

Materialart: Digitale Medien

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