52144-70-4Relevant articles and documents
Bimolecular formation of radicals by hydrogen transfer, 12: Transfer hydrogenation of p-substituted α-methylstyrenes and of 9-methylenefluorene as a criterion of mechanism
Friebolin, Heike,Roers, Rolf,Ebenhoch, Jochen,Gerst, Matthias,Ruechardt, Christoph
, p. 385 - 389 (1997)
The uncatalyzed transfer hydrogenation of substituted α-methylstyrenes with 9,10-dihydroanthracene (DHA), xanthene (XAN), or 9,10-dihydroacridine (DHAC) was studied mechanistically. The three hydrogen donors react at very similar rates and with similar activation parameters and with little discrimination between the various substituted styrenes. The kinetic isotope effects are also similar and the solvent effect is small. A hydrogen atom transfer mechanism (retrodisproportionation) is, therefore, preferred to a hydride transfer mechanism. This is supported by the very similar reactivity of the hydrogen transfer reaction of DHA and XAN with 9-methylenefluorene. The product yields in all reactions investigated in this project were >90%. VCH Verlagsgesellschaft mbH, 1997.
Heterogeneous Catalytic Hydroarylation of Olefins at a Nanoscopic Aluminum Chlorofluoride
Calvo, Beatriz,Wuttke, Jan,Braun, Thomas,Kemnitz, Erhard
, p. 1945 - 1950 (2016/07/06)
We report on hydroarylation reactions of arenes with olefins under very mild conditions catalyzed heterogeneously by aluminum chlorofluoride (ACF; AlClxF3?x, x≈0.05–0.25). The reactions of benzene and toluene with ethylene or propylene proceed with high conversions to afford various alkylated arenes. For cyclohexene and 1-hexene, the reactions require higher temperatures and the conversions are lower. ACF also catalyzes the hydroarylation of 1,3,5-trifluorobenzene and pentafluorobenzene with ethylene and propylene. The alkylations of arenes with non-fluorinated olefins resemble typical Friedel–Crafts chemistry to give rise to Markovnikov regioselectivity. The reaction of CF3CH=CH2 with benzene proceeds with anti-Markovnikov regioselectivity to give the fluorinated olefin PhCHCH=CF2 and the alkylation product PhCH2CH2CF3 as products of C?F and C?H activation.