Carbene‐Stabilized Dithiolene (L0) Zwitterions. (12th September 2021)

• Record Type: Journal Article
• Authors: Wang, Yuzhong; Tran, Phuong M.; Xie, Yaoming; Wei, Pingrong; Glushka, John N.; Schaefer, Henry F.; Robinson, Gregory H.
• Is Part Of: Angewandte Chemie. Volume 133:Number 42(2021)
• Page Start: 22888
• Page End: 22892
• Publication Date: 2021-09-12
• Subjects: carbenes -- dithiolenes -- silicon -- silylenes -- sulphur; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202108498
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A series of reactions between Lewis bases and an imidazole‐based dithione dimer (1 ) has been investigated. Both cyclic(alkyl)(amino)carbene (CAAC) (2 ) and N‐heterocyclic carbene (NHC) (4 ), in addition to N‐heterocyclic silylene (NHSi) (6 ), demonstrate the capability to cleave the sulphur–sulphur bonds in 1, giving carbene‐stabilized dithiolene (L 0 ) zwitterions (3 and 5 ) and a spirocyclic silicon–dithiolene compound (7 ), respectively. The bonding nature of 3, 5, and 7 are probed by both experimental and theoretical methods. Abstract : Scissions of sulphur–sulphur bonds in an imidazole‐based dithione dimer by stable Lewis bases have been investigated. While NHSi gives a spirocyclic silicon–dithiolene complex, both CAAC and NHC provide unusual carbene‐stabilized dithiolene (L 0 ) zwitterions.