41640-83-9Relevant articles and documents
A de novo synthetic method to the access of N-substituted benzazepines
Ouchakour, Lamiaa,Nonn, Melinda,D'hooghe, Matthias,Kiss, Loránd
, (2020/02/04)
A novel, convenient procedure has been described for the construction of fluorine-containing benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by r
Thermolysis of 3,4-Cyclic 1,2-Dioxetanes: Effect of 6-Ring Conformation on the Activation Parameters
Baumstark, Alfons L.,Vasquez, Pedro C.
, p. 5213 - 5216 (2007/10/02)
2a,3,8,8a-Tetrahydronaphtho-1,2-dioxete (1) and 2a,3,4,8b-tetrahydronaphtho-1,2-dioxete (2) were synthesized by the Kopecky method.The dioxetanes, purified by low-temperature chromatography, were characterized by 1H NMR spectroscopy and by analysis of their thermolysis products.The activation parameters for the termolysis of 1 and 2 in xylenes were determined by the chemiluminescence method a = 27.4 kcal/mol, log A = 14.4, k60 deg = 2.8*10-4 s-1. 2: Ea = 24.5 kcal/mol, log A = 12.8, k60 deg = 5.1*10-4 s-1>.The termal decomposition of both dioxetanes produced (directly) much higher yields of excited triplet carbonyl products than excited singlet products.The total yields of excited states were 1percent for both dioxetanes, much less than normal for disubstituted dioxetanes.Molecular mechanics (MM2) calculations were carried out.The most stable conformation of 1 was predicted to be a boat with a O-C-C-O torsion angle of 0 deg. 3,4-Tetramethylene-1,2-dioxetane (3) was predicted to favor a 'twist-boat' conformation with a dioxetane ring torsion angle of 10 deg.The conformation of 2 was calculated to be intermediate with a dioxetane ring torsion angle of 4 deg.The relative stabilities of the dioxetanes seem to correlate with ring conformation and dioxetane (O-C-C-O) torsion angle.
