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Beilstein J. Org. Chem. 2015, 11, 1–8, doi:10.3762/bjoc.11.1
Graphical Abstract
Figure 1: 2,6,9-Trioxabicyclo[3.3.1]nonadiene (“bisdioxine”) derivatives.
Figure 2: B3LYP/6-31G**-calculated structures of the stable endo,endo diisocyanate 1 (left) and the unstable ...
Scheme 1: Ring opening taking place on attempted optimization of the calculated, putative endo,exo isomer of 1...
Scheme 2: Synthesis of the di(hexylurea) and di(methyl carbamate) derivatives 4 and 5.
Figure 3: Stereoscopic ORTEP plot of molecule A of the di(hexylurea) derivative 4 with atomic numbering schem...
Figure 4: Stereoscopic ORTEP plot of molecule B of 4 with atomic numbering scheme. The ellipsoids are drawn a...
Figure 5: Stereoscopic ORTEP plot of the di(methyl carbamate) 5 showing the atomic numbering scheme. The elli...
Figure 6: The lowest-energy calculated structure of 4 (B3LYP/6-31G**; for other conformers and full details s...
Figure 7: Calculated structure of 5 (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. For a...
Scheme 3: Synthesis of bis-crown ether diamides 7.
Figure 8: Calculated structure of 7a-a (B3LYP/6-31G**). Bond lengths are given in Å and angles in degrees. Fo...
Figure 9: Calculated structure of 7b-a (B3LYP/6-31G**). For other conformers (7b-b and 7b-c) and full details...
Beilstein J. Org. Chem. 2013, 9, 754–760, doi:10.3762/bjoc.9.85
Scheme 1: Phenylnitrene–2-pyridylcarbene rearrangement.
Scheme 2: Type I and type II ring opening and ring expansion in 3- and 2-pyridylnitrenes, respectively.
Scheme 3: FVT reactions of 4-azidopyridine (18), 2-(5-tetrazolyl)pyrazine (23) and triazolo[1,5-a]pyrazine (24...
Figure 1: Difference-IR spectrum of 2-diazomethylpyrazine (22) (positive peaks) in Ar matrix at 7 K, obtained...
Figure 2: Ar matrix IR-difference spectra showing the products of broadband UV photolysis of 4-azidopyridine (...
Figure 3: Top: calculated IR spectrum of 20 at the B3LYP/6-31G* level (wavenumbers scaled by 0.9613): ν’ (rel...
Figure 4: Bottom: IR spectrum from the matrix photolysis of azide 18 after the azide has been depleted comple...
Scheme 4: Photolysis reactions of azide 18 and triazole 24 in Ar matrix.
Beilstein J. Org. Chem. 2013, 9, 743–753, doi:10.3762/bjoc.9.84
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.