Oxidation of phenols to ortho-quinones using diphenylseleninic anhydride

Abstract

SW7 2AY)Su~zmnry Phenols, including examples with an unblocked para-position, are oxidised to the corresponding orthoquinones using diphenylseleninic anhydride.

Synthese von (+)‐Taxodion

“…2 (s, C-4), 50.2 (d, C-5), 52.4 (q, C-21), 109.7 (d, C-ll), 123.5 (s, C-6), 124.3 (d, C-14), 125.9 (s, C-8), 131.8 (s, C-13), 131.9 (d, C-7), 145.2 (s, C-9), 152.8 (s, C-12), 179.4 (s, C-20). (12), 225 (21), 213 (20), 197 (10).…”

On the Functionalization of [2.2](1,4)Phenanthrenoparacyclophane

“…The phenols 29a / b are interesting chiral cyclophane derivatives in their own right, but also offer themselves for oxidation to the corresponding quinones. Treating 29a with benzeneseleninic anhydride18 indeed affords the ortho ‐quinone 31 in acceptable yield, accompanied by small amounts of its para isomer 30 (Scheme ). The two compounds were separated by plate chromatography and characterized by their spectroscopic data (see Experimental Section); 30 crystallizes in form of beautiful, deep black prisms.…”

Quinone studies. Part III. Metal ion-catalysed oxidation of halophenols and halonaphthols by peroxidisulphate

“…The yields of single compounds in most cases are poor. Fremy's salts (Teuber and Rau 1953;Teuber and Staiger 1955) thallium trifluoro acetate (McKillop et al 1970), hydrogen peroxide hydrochloric acid (Perumal and Bhatt 1979), periodic acid (Perumal and Bhatt 1979), cerium IV oxide-hydrogen peroxide (Barton et al 1975), and diphenyl seleninic anhydride (Barton et al 1976(Barton et al , 1977 are reagents which give quinones.…”