Preparation and solid state characterization of 1,2,3,5-diselenadiazolyl [HCN2Se2]?

The reaction of selenium dichloride with divinyl sulfide

“…Selenium dichloride has been obtained by disproportionation of selenium and SeCl 4 and used for the preparation of diselenadiazolium chloride, a compound with a N-Se bond [5,6]. A complex of SeCl 2 with tetrahydrothiophene has been synthesized and characterized by X-ray analysis [7].…”

The Synthesis and Characterization of Stable Radicals Containing the Thiazyl (SN) Fragment and Their Use as Building Blocks for Advanced Functional Materials

“…92,134 Studies on diselenadiazolyl radicals 45 are more limited compared to their sulfur counterparts 35 owing, in part, to the lower solubility and thermal stability of the former. The few EPR spectra which have been reported 86,134 consist of a broad featureless singlet; g-values for 45 are consistently higher than for the sulfur analogues 35, as anticipated for radicals with substantial spin density on selenium. Computational and experimental studies on the prototypical diselenadiazolyl radical (R = H) point to an electronic structure analogous to that for the corresponding sulfur-based radical.…”

“…Nearly all of the structurally characterized diselenadiazolyl radicals adopt the cofacial π dimer structure, including R = phenyl, 86 cyanophenyl, 92,135 2,5-diflurophenyl, 99 5-cyano-2-furyl, 136 and R = hydrogen. 134 The methyl derivative adopts a twisted structure analogous to its sulfur analogue. 137 Several diselenadiazolyl diradicals also adopt the superimposed π dimer structure; the 1,4-, 123 1,3-, 126 and 5-cyano-1,3-phenylene-bridged 127 diradicals are all isostructural with their dithiadiazolyl counterparts (see above), and the 1,3-phenylene-bridged diradical also exists as a second polymorph in which the diradicals exist as discrete dimers instead of the zigzag extended structure.…”

“…This compound is a markedly better conductor than most of the other monofunctional RCN 2 Se 2 radicals. 134 Similarly, the dithiadiazolyl diradical 39, which has "no" substituent, is one of the few dithiadiazolyl radicals with measurable conductivity. 121,122 Both of these radical derivatives have π stacks of cofacial π dimers as well as extensive interstack contacts.…”

Addition of selenium dibromide to divinyl sulfide: spontaneous rearrangement of 2,6-dibromo-1,4-thiaselenane to 5-bromo-2-bromomethyl-1,3-thiaselenolane

“…3 Selenium dichloride was used for the preparation of several compounds not containing a carbon-selenium bond. [5][6][7][8][9] In the reaction with N,N-bis(trimethylsilyl)-2,6-diisopropylaniline, selenium dichloride underwent disproportionation to Se 2 Cl 2 and selenium tetrachloride, which was involved in the electrophilic aromatic substitution reaction. 10 We reported previously the synthesis of an organoselenium compound using SeCl 2 and SeBr 2 via the addition of the selenium dihalide to dimethyl diethynyl silane.…”