Thermolysis and photochemistry of cyclic azo compounds. A novel chemiluminescent reaction and alternate route to Dewar benzene

Intramolecular triplet energy transfer in ester-linked bichromophoric azoalkanes and naphthalenes

“…Found: 239.0909. 5-Carboxy-2,3-diazabicyclo[2.2.2]oct-2-ene (10). The above hydrogenated adduct (8.2 g, 0.034 mol), solid 85% KOH (9.8 g, 0.15 mol), and 80 mL of z-PrOH were refluxed under N2 for 16 h. After cooling to room temperature, the salts were filtered off and washed with MeOH.…”

“…5-Benzoyl-2,3-diazabicyclo[2.2.2]oct-2-ene (AP-DBO). The DBO acid (10) (1.36 g, 8.83 mmol) was converted to the sodium salt by dissolution in enough 0.1 N NaOH to keep the solution basic. The water was removed by rotary evaporation and the sodium salt was evacuated at 120 °C for 2 h. The salt was suspended in 20 mL of dry benzene in a flask equipped with a reflux condenser and nitrogen inlet.…”

Deazetation of a bicyclic azo compound: product and mechanistic studies

“…Inter-system Crossing.-Inter-system crossing from lnR* azo compounds is generally a fairly slow process,'*21 though, in a few cases, it is believed to compete with loss of nitrogen. 22 In the present case, Scheme 7 would imply that the 'singlet product distribution' is given by the thermolysis data extrapolated to the photolysis temperature, as above. Further, the 'triplet product distribution' would be given by the sensitised photolysis.…”

Synthesis of nickel(II) isobacteriochlorins from nickel(II) complexes of chlorophyll derivatives

“…In the case of -meso-methyl free-base 3a, the 10a,b-H were too closely coupled to allow an analysis. "Concentrations (CDC13; mM): 8a (7.0), 9b (8.1), 5 (5.4). 6 Assignment of the 7a,b-CH2CH2 by analogy to 8a.15 Assignments of these pairs may be interchanged.…”