55894-48-9Relevant articles and documents
Transformations photochimiques d'endoperoxydes derives d'hydrocarbures aromatiques polycycliques II. Cas de l'endoperoxyde d'anthracene: di- et tetraepoxydes derives
Defoin, Albert,Baranne-Lafont, Joele,Rigaudy, Jean
, p. 145 - 155 (2007/10/02)
Syn 4a,10:9,9a-diepoxy-4a,9,9a,10-tetrahydroanthracene 10, an intermediate in the thermal transformations of 9,10-epidioxyanthracene 5a, can be prepared by photolysis of 5a in benzene at long wavelengths (λ >/= 435 nm) and at low temperature.Its chemical behaviour has been studied.In particular, diepoxide 10 appears to be very sensitive to acids and is isomerized by ZnCl2 into a bicyclic acetal: 6,11-epoxy-6,11-dihydrodibenzooxepine 20.Acetal 20 is itself isomerized by CF3CO2H into the unstable 1-(2-hydroxyphenyl)-isobenzofuran 32, which can be trapped by N-methylmaleimide as endo (33) and exo (35) adducts.Photo-oxygenation of die 10 leads to the 1,4-epidioxy-4a,10:9,9a-diepoxy-1,4,4a,9,9a,10-hexahydroanthracenes, syn 25 and anti 26, which by thermal or photochemical isomerization give the 1,2:3,4:4a,10:9,9a-tetraepoxy-1,2,3,4,4a,9,9a,10-octahydroanthracenes syn 27 and anti 28.The stereochemistry of these new compounds has been deduced from 1H NMR spectra.