Synthesis, Structure, and Reactivity of Organochalcogen (Se, Te) Compounds Derived from 1-(N,N-Dimethylamino)naphthalene andN,N-Dimethylbenzylamine

• DOI: 10.1021/om9808312
• Publication Date: 2002-07-26T05:43:16Z
• Authors: Arunashree Panda; G. Mugesh; Harkesh B. Singh; Ray J. Butcher
• Keywords: Asymmetric Methoxyselenenylation; Nmr-Spectroscopy; Monomeric Selenolato Complexes; 540; 01 natural sciences; Diferrocenyl Dichalcogenides; 0104 chemical sciences; Glutathione-Peroxidase; Crystal-Structures; Amino Group; Spectroscopic Characterization; Molecular-Structure; Chiral Selenium-Compounds

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)...