Facile synthesis of benzimidazolin-2-chalcogenones: Nature of the carbon–chalcogen bond

Redox Reaction between Main‐Group Elements (Te, Sn, Bi) and N‐Heterocyclic‐Carbene‐Derived Selenium Halides: A Facile Method for the Preparation of Monomeric Halides

“…In view of the different reactivity of dihalobenzimidazolin‐2‐selones relative to the dihaloimidazolin‐2‐selones with elemental tellurium as reported by Devillanova and co‐workers,14a the structural features have been interpreted 34,35. The C–Se bond in the benzimidazolin‐2‐selone system is stronger than that in imidazole‐2‐selones,34 and this might be the reason for the poor reactivity of benzimidazolin‐2‐selones, which are not further oxidized to cationic diselenides.…”

“…Precursor selones 4a and 4b were synthesized by treating 3‐(2‐bromobenzyl)‐1‐butyl‐1 H ‐benzo[ d ]imidazol‐3‐ium bromide and 3‐(2‐bromobenzyl)‐1‐isopropyl‐1 H ‐benzo[ d ]imidazol‐3‐ium bromide with Na 2 Se 2 (prepared in situ) in the presence of potassium tert ‐butoxide, respectively 34. Similarly, N , N′ ‐alkylated benzimidazolin‐2‐selones 4c , 4d , and tellone 4i were synthesized by treating Na 2 Se 2 with 1,3‐dibutyl‐1 H ‐benzo[ d ]imidazol‐3‐ium bromide and 1,3‐diisopropyl‐1 H ‐benzo[ d ]imidazol‐3‐ium bromide and Na 2 Te 2 with 1,3‐dibutyl‐1 H ‐benzo[ d ]imidazol‐3‐ium bromide, respectively.…”

Recent Advances in the Field of Main‐Group Mono‐ and Diatomic “Allotropes” Stabilised by Neutral Ligands

“…A recent paper on the topic proposed a distinct CÀCh double bond for these species (28 b). [52] An in-depth study on the bonding in these species in the context of an analogy to NHC-stabilised E 1 compounds might be interesting; that is, as a donor-acceptor complex with a significant degree of p backbonding. Theoretical studies: Two recent theoretical studies have explored the possibility of extending the L-E-E-L concept to Group 2.…”

An Efficient Synthesis of 1,3-Dialkylimidazole-2-Selenones

“…7 In addition, 1,3-dialkylimidazole salts also react with Na 2 Se 2 at room temperature in dry THF using potassium tert-butoxide as a base to afford the target products. 8,9 Both Roy 10 and Guziec 11 reported that treatment of imidazole with BuLi and selenium powder also gave 1,3-dialkylimidazole-2-selenones under Schlenk conditions. However, most of the known methods for the preparation of imidazole-2-selenones suffer from disadvantages such as use of strong bases and harsh reaction conditions, long reaction time, low yields or complicated work-up.…”