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Beilstein J. Org. Chem. 2013, 9, 743–753, doi:10.3762/bjoc.9.84
Graphical Abstract
Scheme 1: 4-Pyridylnitrene–2-pyrazinylcarbene interconversion.
Scheme 2: Ring expansion and ring contraction in 2-pyridylnitrene (4).
Scheme 3: Ring opening and ring expansion in 3-pyridylnitrene (10).
Scheme 4: Ring opening and ring contraction in 3-pyridylnitrene (10) and diazacycloheptatetraene 16.
Figure 1: Energy profile for the ring opening and ring contraction in 3-pyridylnitrene 10 and 1,6-diazacycloh...
Scheme 5: Potential direct ring contraction in 3-pyridylnitrene (10).
Scheme 6: Ring contraction by ring opening to nitrile ylide 11.
Scheme 7: Generation of pyrimidinyldiazomethanes and pyrimidinylcarbenes.
Scheme 8: Formation of cyanopyrroles by FVT of tetrazolylpyrimidines.
Scheme 9: Rearrangements of pyrimidinylcarbenes to cyanopyrroles via nitrile ylides 31 and 37.
Scheme 10: Rearrangements of phenyl(dimethylpyrimidinyl)carbene.
Scheme 11: Photolysis of 3-azido-2-phenylquinoline.
Figure 2: IR difference spectra from the photolysis of 3-azido-2-phenylquinoline (44) in Ar matrix. (a) Calcu...
Figure 3: UV–vis spectra from the sequential photolysis of 3-azido-2-phenylquinoline (44) in Ar matrix at 310...
Scheme 12: Preparative FVT of 3-azido-2-phenylquinoline.
Scheme 13: FVT of 2-phenyl-4-quinazolinylcarbene precursors.