A singlet aryl-CF3 carbene: 2-benzothienyl(trifluoromethyl)carbene and interconversion with a strained cyclic allene.
Matrix-isolated 2-benzothienyl(trifluoromethyl)carbene was generated by irradiation of the corresponding diazirine, and characterized by IR and UV/vis spectroscopy, in situ trapping, and DFT modeling. Experiments and calculations indicate that the carbene is a ground-state singlet, in contrast to previously characterized aryl(trifluoromethyl)carbenes. The carbene could be interconverted photochemically with a ring-opened thioquinomethide and a highly strained cyclic allene.
Wang
Jian
J
Department of Chemistry, Mail Stop 216, University of Nevada, Reno, Nevada 89557, USA.
Sheridan
Robert S
RS
D000345:Affinity Labels / Q000138:chemical synthesis*; D000466:Alkadienes / Q000737:chemistry; D003978:Diazomethane / Q000737:chemistry / Q000528:radiation effects; D006838:Hydrocarbons / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000345:Affinity Labels; D000466:Alkadienes; D006838:Hydrocarbons; D006845:Hydrocarbons, Fluorinated; C030011:carbene; C025947:propadiene; D003978:Diazomethane; D008697:Methane