35310-83-9Relevant academic research and scientific papers
Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
Liu, Guangchang,Xu, Bo
supporting information, p. 869 - 872 (2018/02/09)
We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
Photochemically generated bicyclic ortho-quinodimethanes: Photo- enolization of bicyclic aldehydes and ketones
Connolly, Terrence J.,Durst, Tony
, p. 15969 - 15982 (2007/10/03)
A photoenolization route to bicyclic ortho-quinodimethanes was investigated. Bicyclic photoenols were trapped in an intermolecular fashion with various dienophiles for the first time. All ortho-quinodimethane precursors were prepared via a selective route commencing with 1-indanol, α- tetralol and 1-benzosuberone. Irradiation afforded the E-photoenols exclusively which were trapped with equal efficiency except that derived from indane-4-carboxaldehyde. This low efficiency has been ascribed to rapid auto- oxidation of the aldehyde to carboxylic acid. The facial selectivity of the reaction between the photoenol from benzosuberan-9-carboxaldehyde and dimethyl fumarate was much lower when compared to the other aldehydes in this study. A distorted diene caused by the presence of the seven membered ring explains these results.
