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Facile Conversion of Bis-Silylene to Cyclic Silylene Isomers: Unexpected C-N and C-H Bond Cleavage.
- Source :
-
Journal of the American Chemical Society . 11/15/2017, Vol. 139 Issue 45, p16109-16112. 4p. - Publication Year :
- 2017
-
Abstract
- Reaction of thiolate 1 with carbene-stabilized diiodo-bis-silylene (2) (in a 2:1 ratio) in THF unexpectedly gives both the first five-membered, sulfur-containing, zwitterionic silylene ring (3) via insertion of the "Si2I" unit of 2 into the olefinic C--H bond of the imidazole ring of 1 and four-membered cyclic silylene (4) via insertion of a silicon(I) atom of 2 into the Cphenyl--N bond of the carbene ligand. The parallel reaction in toluene only gives 3 as the major product. The nature of the bonding in isomeric 3 and 4 was probed by experimental and theoretical methods. [ABSTRACT FROM AUTHOR]
- Subjects :
- *SILICON
*HYDRIDES
*CHEMICAL reactions
*HETEROCYCLIC compounds
*SILYLENES
Subjects
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 139
- Issue :
- 45
- Database :
- Academic Search Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 126380023
- Full Text :
- https://doi.org/10.1021/jacs.7b10325