Wavelength-Dependent Selectivity in [4 + 4]-Cycloaddition Reactions
摘要:
Selective excitation of a variety of anthracene derivatives in the presence of anthracene led to the formation of only the cross-cyclomer products, while irradiating these mixtures at wavelengths where anthracene also absorbs led to both dianthracene and the mixed cyclomers being formed. This method was shown to be general, so long as the chromophore was inert toward forming its homodimer and could be irradiated at wavelengths at which anthracene does not absorb.
Synthesis and Photodimerization of 2- and 2,3-Disubstituted Anthracenes: Influence of Steric Interactions and London Dispersion on Diastereoselectivity
作者:Thomas Geiger、Anne Haupt、Cäcilia Maichle-Mössmer、Claudio Schrenk、Andreas Schnepf、Holger F. Bettinger
DOI:10.1021/acs.joc.9b01317
日期:2019.8.16
of the size of primary alkyl substituents in 2- and 2,3-positions of anthracenes on the diastereoselectivity (anti vs syn dimer) of the [π4s + π4s] photoinduced dimerization is investigated. The synthesis of the anthracene derivatives was achieved by Suzuki–Miyaura reaction of 2,3-dibromoanthracene with alkylboronic acids as well as by reduction of anthraquinones that were obtained from 2,3-disubstituted
Synthesis of Anthracene and Azaanthracene Fluorophores via [2+2+2] Cyclotrimerization Reactions
作者:Yan Zou、Douglas D. Young、Alejandra Cruz-Montanez、Alexander Deiters
DOI:10.1021/ol8019549
日期:2008.10.16
A highly convergent [2+2+2]-cyclotrimerization approach to anthracenes and 2-azaanthracenes has been developed. It allows for the facile introduction of the anthracene moiety on alkyne and nitrile bearing molecules and the rapid construction of compound arrays. This is showcased in the assembly of a collection of fluorophores and their photochemical evaluation.