J. Nakayama, I. Akiyama, A. Sugihara
Sep 19, 1998
Citations
0
Influential Citations
14
Citations
Journal
Journal of the American Chemical Society
Abstract
Treatment of 1-chloro-2,2-bis(diethylamino)ethene (1) with elemental selenium in refluxing benzene gave 4,8-bis[bis(diethylamino)methylene]-1,2,3,5,6,7-hexaselenacyclooctane (4) in 60% yield. The structure of 4 was determined by X-ray diffraction analysis. Compound 4 behaves as 2,2-bis(diethylamino)-2-ethylium-1-diselenocarboxylate (3) toward a range of reagents. Thus, 4 reacted with MeI, dimethyl acetylenedicarboxylate, and elemental sulfur, under mild conditions, to give the carbenium iodide 5a, the 1,3-diselenole 6a, and the dithiocarboxylate 2, respectively, in high yields, while the thermolysis in refluxing o-dichlorobenzene afforded the α-diselenoamide 7. Evidence for the dissociation of 4 into 3 in solution is provided by IR, UV/vis, and 1H-, 13C-, and 77Se-NMR spectra.