Interaction of 9-substituted anthracenes with oxidation systems tert-butylhydroperoxide-metal tert-butoxide

Stepovik, L. P.; Malysheva, Yulia B.; Fukin, Georgy K.

doi:10.1134/s1070363215060080

Cited by 2 publications

(1 citation statement)

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“…A search in the same database for the 10-hydroxy anthrone fragment resulted in 59 hits, of which 10 structures had an aromatic ring at the 10-position, namely refcodes COBWEY (Barker et al, 2019), DULVUB (Skrzat & Roszak, 1986), ELULII (Stepovik et al, 2015), EVETIL (Mao et al, 2021), JAYPAA (Roszak et al, 1990), MOTJIQ (Chen et al, 2015), MOTKEN (Chen et al, 2015), QAJPUQ (Forensi et al, 2020), SAMNEC (Hoffend et al, 2013) and WOKYIH (Pullella et al, 2019). The anthrone unit in these 10 structures are either essentially planar or in a shallow boat conformation.…”

Section: Database Surveymentioning

confidence: 99%

Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product

Weaver

Campbell

et al. 2022

Acta Cryst E

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The syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitroanthracen-9-yl)isoxazole-4-carboxylate, C21H16N2O5, (I), and its oxidation product, ethyl 3-(9-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate, C21H17NO5 (V) are described. Compound (I) crystallizes with two molecules in the asymmetric unit in which the dihedral angles between the anthracene fused-ring systems and isoxazole ring mean planes are 88.67 (16) and 85.64 (16)°; both molecules feature a disordered nitro group. In (V), which crystallizes with one molecule in the asymmetric unit, the equivalent dihedral angle between the almost planar anthrone ring system (r.m.s. deviation = 0.029 Å) and the pendant isoxazole ring is 89.65 (5)°. In the crystal of (I), the molecules are linked by weak C—H...O interactions into a three-dimensional network and in the extended structure of (V), inversion dimers linked by pairwise O—H...O hydrogen bonds generate R 2 2(14) loops.

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