5434-98-0Relevant academic research and scientific papers
Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring
Jones, Mathew J.,Callejo, Ricardo,Slawin, Alexandra M. Z.,Bühl, Michael,O'Hagan, David
, p. 2823 - 2827 (2016)
2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of
The effect of Lewis acids on the cycloaddition of 3,3,6-Trimethylcyclohex- 5-ene-1,2,4-trione: Hydrogen transfer versus cycloaddition with cyclopentadiene
Eddy, Nicholas A.,Richardson, Jay J.,Fenteany, Gabriel
, p. 5041 - 5044 (2013/11/06)
Exposure of 3,3,6-trimethylcyclohex-5-ene-1,2,4-trione to catalytic amounts of Lewis acids revealed two disparate reactions in the presence of cyclopentadiene. The expected cycloaddition was found to be reversible for the title compound, and transfer hydrogenation was the preferred pathway over long periods of time. Other tested substrates were able to undergo facile cycloaddition with considerable yields and without the parallel reduction. The work presented here defines the effect of Lewis acid catalysts on the reaction between cyclopentadiene and 3,3,6-trimethylcyclohex-5-ene-1,2,4-trione. Cycloaddition and hydrogenation reactions both occur in parallel. For cycloaddition, the dr was similar for all Lewis acids tested. Hydrogenation was catalyzed efficiently by AlCl3 and found to be the main mode of reaction for this particular system. Copyright
Access to dienophilic ene-triketone synthons by oxidation of diketones with an oxoammonium salt
Eddy, Nicholas A.,Kelly, Christopher B.,Mercadante, Michael A.,Leadbeater, Nicholas E.,Fenteany, Gabriel
supporting information; experimental part, p. 498 - 501 (2012/02/16)
Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diels-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.
