ChemInform Abstract: Selective Oxidation of 1‐Tetralones to 1,2‐Naphthoquinones with IBX and to 1,4‐Naphthoquinones with Oxone® and 2‐Iodobenzoic Acid.

Abstract

Selective Oxidation of 1-Tetralones to 1,2-Naphthoquinones with IBX and to 1,4-Naphthoquinones with Oxone® and 2-Iodobenzoic Acid. -The substituents on the aromatic tetralone ring have a significant effect on the product yields. Oxidation of substrates (III) to the corresponding 1,4-naphthoquinones is unsuccessful. -(REN, J.; LU, L.; XU, J.; YU, T.; ZENG*, B.-B.; Synthesis 47 (2015) 15, 2270-2280, http://dx.

Efficient Oxidative Dearomatisations of Substituted Phenols Using Hypervalent Iodine (III) Reagents and Antiprotozoal Evaluation of the Resulting Cyclohexadienones against T. b. rhodesiense and P. falciparum Strain NF54

“…119.8–121.4 °C). The spectroscopic data were found to be identical to the ones described in Ref [ 73 ]. Although 5d represents an already known compound, to our knowledge the complete assignment of the NMR signals have not been published so far: 1 H NMR (400 MHz, CDCl 3 ): δ = 8.14 (dd, 3 J H,H = 8.6, 4 J H,F = 5.2 Hz, 1H, H-5), 7.73 (dd, 3 J H,F = 8.5, 4 J H,H = 2.6 Hz, 1H, H-8), 7.43 (td, 3 J H,F = 8.5, 3 J H,H = 8.5, 4 J H,H = 2.6 Hz, 1H, H-6), 7.02 (d, J = 10.4 Hz, 1H, H-2), 6.99 (d, J = 10.4 Hz, 1H, H-3) ppm; 13 C NMR (100 MHz, CDCl 3 ): δ = 183.9 (d, 4 J C,F = 1.5 Hz, C-1), 183.6 (d, 5 J C,F = 1.0 Hz, C-4), 166.1 (d, 1 J C,F = 257.6 Hz, C-7), 138.9 (C-3), 138.6 (d, 5 J C,F = 2.0 Hz, C-2), 134.5 (d, 3 J C ,F = 8.0 Hz, C-8a), 129.8 (d, 3 J C,F = 9.0 Hz, C-5), 128.5 (d, 4 J C,F = 3.3 Hz, C-4a), 121.2 (d, 2 J C,F = 22.6 Hz, C-6), 113.2 (d, 2 J C,F = 23.6 Hz, C-8) ppm.…”

“…Amber solid; yield: 87%; R f = 0.46 (cyclohexane:EtOAc = 3:1); m.p. : 119–120 °C (lit [ 73 ] m.p. 119.8–121.4 °C).…”