Oxidation of alkoxphenols. Part XIII. Oxidation of t-butylated resorcinol monoethers and related compounds

Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase

“…The solvent was removed under vacuum and the residue was purified by column chromatography using light petroleum (60-80 • C)-ethyl acetate (80 : 20) as eluent to give the title compound 12c as a white solid (1.010 g, 41%), mp 46-47 • C (lit. 24 mp 54-55 • C); m max (film)/cm −1 3542, 3433 (OH), 1600 (C=C); d H (300 MHz; CDCl 3 ) 1.22 (9H, s, C(CH 3 ) 3 ), 3.61 (3H, s, OCH 3 ), 3.71 (3H, s, OCH 3 ), 6.43 (1H, s, H-6), 6.70 (1H, s, H-3); d C (75 MHz; CDCl 3 ) 30.6 (CH 3 , C(CH 3 ) 3 ), 34.9 (quat., C(CH 3 ) 3 ), 56.1 (OCH 3 ), 57.3 (OCH 3 ), 100.9 (CH, C-6), 111.2 (CH, C-3), 130.1 (quat., C-4), 139.9 (quat. ), 144.6 (quat.…”

On the Significance of the Superoxide Radical () in Oxidative Delignification, Studied with 4-t-Butylsyringol and 4-t-Butylguaiacol. Part I. The Mechanism of Aromatic Ring Opening

“…The model compounds, 4-f-butylsyringoI (1) and 4-f-butyIguaiacol (2), were synthesized according to known methods (Rosenwald 1952;Ley and M ller 1956;Adderley and Hewgill 1968) and the structure and purity were confirmed by HPLC, GC-MS and NMR. Milli-Q (Millipore) filtered water was used s solvent.…”

Phenanthrene-4,5-quinones: a synthesis of morphenol

“…Solutions of the oxepine (19) became blue as the equilibrium with the quinone (9) was re-established. Catalytic hydrogenation regenerated the diol (8). Thus, in every respect the quinone (9) resembles a dipheno-2,2'-quinone, in which the rings are locked in a ( 2 ) configuration.…”

“…To preclude this preference for intramolecular ether formation the hydroxy groups were temporarily locked on the same side of the molecule by formation of the cyclic sulphite ester (16). This was then photobrominated, and the bisbromomethyl compound (17) treated with magnesium to give the dihydrophenanthrene (18), which was hydrolysed to the diol (8).…”