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Beilstein J. Org. Chem. 2012, 8, 958–966, doi:10.3762/bjoc.8.108
Graphical Abstract
Scheme 1: Dihydroazulene (DHA)/vinylheptafulvene (VHF) photo-/thermoswitch.
Figure 1: Numbering of azulene.
Scheme 2: Bromination–elimination protocol for functionalization of DHA [3,5-8]. HMDS = hexamethyldisilazide.
Scheme 3: Bromination of VHF [11]. NBS = N-bromosuccinimide.
Scheme 4: Radical and ionic brominations of VHF.
Figure 2: 1H,1H COSY NMR spectrum of DHA 8 (CDCl3, 500 MHz). For assignments of DHA signals, see numbering in ...
Figure 3: Molecular structures (with displacements ellipsoids at 50% probability for non-H atoms) of (a) DHA 8...
Figure 4: 1H NMR spectra (C6D6, 300 MHz) of (a) DHA 1; (b) VHF 2; (c–e) VHF 2 after treatment with 2 molar eq...
Figure 5: Compound 9 was selectively brominated to furnish the product 10.
Scheme 5: Synthesis of 3,7-dibromo-DHA.
Scheme 6: Synthesis of a 3,7-dibromoazulene.
Scheme 7: Regioselective Sonogashira and Suzuki couplings. RuPhos = 2-dicyclohexylphosphino-2',6'-diisopropox...
Scheme 8: Slow conversions to azulenes in the solid state.
Figure 6: Absorption spectra of DHA 8 and VHF 7 in cyclohexane. The broken curve shows the absorption spectru...