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• W2023241578 abstract "A series of intramolecularly coordinated organochalcogen compounds incorporating the 8-(dimethylamino)-1-naphthyl and 2-[(dimethylamino)methyl]phenyl groups has been synthesized. All the compounds were synthesized using the ortholithiation methodology. Insertion of elemental selenium into the Li−C bond of RLi (6) (R = 8-(dimethylamino)-1-naphthyl) afforded the lithium areneselenolate RSeLi (7). Oxidative workup of 7 yielded the yellow diselenide 8 in good yield. Reaction of 8 with a stoichiometric amount of sulfuryl chloride gave the monochloro derivative (9). Controlled bromination of diselenide (8) with bromine in carbon tetrachloride gave the stable selenenyl bromide (10). Compound 8 underwent facile reaction with a stoichiometric amount of iodine to give the corresponding novel monoiodo compound (11) in which selenium is covalently bonded to iodine. Attempts to synthesize the chalcogenides, R2E, 12 (E = Se) and 13 (E = Te), by the reaction of 6 with Se(dtc)2 and Te(dtc)2 (dtc = diethyldithiacarbamate), respectively, were unsuccessful. The reaction of 6 with Te(dtc)2 afforded the stable RTe(dtc) (14) instead of the expected telluride R2Te (13). In contrast, the reaction of R‘Li (17) (R‘ = 2-[(dimethylamino)methyl)phenyl] with Se(dtc)2 and Te(dtc)2 afforded the expected selenide R‘2Se (18) and telluride R‘2Te (19), respectively, in moderate yields. The compounds were characterized by elemental analysis, NMR (1H, 13C, 77Se, 125Te), and mass spectral techniques. The structures of the compounds 9, 11, 14, and 18 were determined by X-ray crystallography. Although N···E (E = Se or Te) nonbonded interactions are present in the solid state in all the derivatives, in solution the pyramidal inversion at the nitrogen center is not blocked, and as a result, the NMe2 signals are observed as sharp signals in the 1H NMR spectra." @default.
• W2023241578 created "2016-06-24" @default.
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• W2023241578 date "1999-04-21" @default.
• W2023241578 modified "2023-10-10" @default.
• W2023241578 title "Synthesis, Structure, and Reactivity of Organochalcogen (Se, Te) Compounds Derived from 1-(<i>N</i>,<i>N</i>-Dimethylamino)naphthalene and <i>N</i>,<i>N</i>-Dimethylbenzylamine" @default.
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• W2023241578 doi "https://doi.org/10.1021/om9808312" @default.
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