1727-63-5Relevant academic research and scientific papers
Generation of Chlorofluorocarbene by Dehalogenation of Fluorotrichloromethane with Reduced Titanium. A New Synthesis of 1-Chloro-1-fluorocyclopropanes.
Dolbier, William R.,Burkholder, Conrad R.
, p. 6749 - 6752 (1988)
Reaction of fluorotrichloromethane with reduced titanium at 0 deg C produces chlorofluorocarbene which adds to alkenes, giving 1-chloro-1-fluorocyclopropanes in good yield
Laser flash photolysis study of chlorofluorocarbene
Tippmann, Eric M.,Platz, Matthew S.
, p. 8547 - 8551 (2003)
10-exo-Fluoro-10′-endo-chlorotricylco[4.3.1.01,6]decadi ene-2,4 (1) was synthesized. Continuous photolysis of 1 (300 nm) generates chlorofluorocarbene 2, which can be intercepted with tetramethylethylene (TME) to form the expected cyclopropane 3. Laser flash photolysis (LFP) of 1 (308 nm) in cyclohexane at ambient temperature does not result in the direct detection of 2 by time-resolved UV-vis spectroscopy. However, LFP of 1 in the presence of pyridine produces the intense transient absorption of ylide 4 at 450 nm. The absolute rate constant of reaction of 2 with pyridine is 8.0 × 109 M-1 s-1 in cyclohexane. LFP (266 nm) of 1 in heptane at ambient temperature produces a transient species with a C-F vibration at 1142 cm-1 and a lifetime of 2.5 μs at ambient temperature. The carrier of the transient absorption is assigned to carbene 2 on the basis of density functional theory (DFT) calculations and on the basis of its kinetic behavior. The absolute rate constant of reaction of carbene 2 with TME was determined by monitoring the transient absorption of ylide 4 (Freon-113) or by time-resolved IR spectroscopy (heptane) to give values of 1.1 × 108 M-1 s-1 and 2.9 × 108 M-1 s-1, respectively. This is the first measurement of a bimolecular ground-state singlet carbene reaction by both time-resolved UV-vis and IR spectroscopy. The value determined by the time-resolved IR measurement is more accurate than that from the ylide probe technique.
Reductive addition of trichlorofluoromethane to ketones initiated by the Mg/LiCl system
Hu, Chang-Ming,Tu, Ming-Hu
, p. 9 - 10 (1994)
Reductive addition of trichlorofluoromethane to ketones initiated by the Mg/LiCl system at -20 deg C to -15 deg C gave dichlorofluoromethyl carbinols in moderate yield.
Thermal cyclopropyl—allyl rearrangement of gem-chlorofluorocyclopropanes under gas-phase pyrolysis conditions. Formation of chlorofluoroalkenes and 2-fluorobuta-1,3-dienes
Volchkov,Lipkind,Nefedov
, p. 1391 - 1401 (2019/08/12)
The gas-phase pyrolysis of isomeric 2-chloro-2-fluoro-1-phenylcyclopropanes in a flow reactor at 250–430 °С gives 1-phenyl- and 3-phenyl-3-chloro-2-fluoropropenes. Under similar conditions, methyl-substituted gem-chlorofluorocyclopropanes undergo cyclopropyl—allyl isomerization accompanied by dehydrochlorination to form chlorofluoroalkenes and 2-fluoro-buta-1,3-dienes.
Addition of CFCl3 to aromatic aldehydes via in situ Grignard reaction
Barkakaty, Balaka,Talukdar, Bandana,Lokitz, Bradley S.
, p. 15098 - 15107 (2015/09/21)
Synthetic modification of trichlorofluoromethane (CFCl3) to non-volatile and useful fluorinated precursors is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the r
Enthalpy versus entropy in chlorocarbene/alkene addition reactions
Moss, Robert A.,Wang, Lei,Zhang, Min,Skalit, Christopher,Krogh-Jespersen, Karsten
, p. 5634 - 5635 (2008/12/20)
We report the first measured activation parameters for the additions of CCl2 and CClF to simple alkenes and demonstrate the existence of enthalpic barriers for CCl2 additions to cyclohexene and 1-hexene. With these two alkenes, addit
Chlorofluorocarbene from Reaction of Fluorotrichloromethane with Reduced Titanium. Synthesis of 1-Chloro-1-fluorocyclopropanes
Dolbier, William R.,Burkholder, Conrad R.
, p. 589 - 594 (2007/10/02)
Generation of chlorofluorocarbene by reaction of CFCl3 with reduced titanium at O deg C, in the presence of various alkenes, produces 1-chloro-1-fluorocyclopropanes in good yield.Evidence from the syn/anti product ratios, including generation of chloroflu
