Facile Conversion of Bis-Silylene to Cyclic Silylene Isomers: Unexpected C-N and C-H Bond Cleavage

Journal of the American Chemical Society
Yuzhong WangGregory H Robinson

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 "SiI2" 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.

References

Oct 21, 2000·Accounts of Chemical Research·M HaafR West
May 4, 2006·Angewandte Chemie·Cheuk-Wai SoRainer B Oswald
Jul 27, 2006·Journal of the American Chemical Society·Matthias DriessDieter Lentz
May 5, 2007·Accounts of Chemical Research·Rory WatermanT Don Tilley
Aug 23, 2008·Science·Yuzhong WangGregory H Robinson
Nov 27, 2008·Chemistry : a European Journal·Erica BrendlerJörg Wagler
Jul 28, 2009·Chemical Reviews·Yoshiyuki MizuhataNorihiro Tokitoh
Jul 9, 2010·Journal of the American Chemical Society·Anukul JanaCarola Schulzke
Jun 4, 2011·Inorganic Chemistry·Yuzhong Wang, Gregory H Robinson
Jan 24, 2012·Angewandte Chemie·Merle ArrowsmithMary F Mahon
Mar 27, 2012·Journal of the American Chemical Society·Andrey V ProtchenkoSimon Aldridge
Mar 27, 2012·Journal of the American Chemical Society·Brian D RekkenPhilip P Power
Aug 3, 2012·Angewandte Chemie·David SchmidtUdo Radius
Mar 29, 2014·Chemistry : a European Journal·Tongen Wang, Douglas W Stephan
Apr 26, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Kalon J IversenJason L Dutton
May 12, 2015·Chemistry : a European Journal·Sabrina PietschTodd B Marder
Dec 18, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Sabrina Würtemberger-PietschTodd B Marder
Jul 29, 2016·Journal of the American Chemical Society·Hunter P HickoxGregory H Robinson
Nov 20, 2016·Angewandte Chemie·Tomoyuki KosaiTakeaki Iwamoto
May 10, 2017·Journal of the American Chemical Society·Yuzhong WangGregory H Robinson

❮ Previous
Next ❯

Citations

Nov 7, 2020·Angewandte Chemie·Arne MerschelRajendra S Ghadwal
Nov 17, 2020·Angewandte Chemie·Maximilian RangHolger Braunschweig
Jul 4, 2018·Chemical Reviews·Vitaly NesterovShigeyoshi Inoue

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Journal of the American Chemical Society
Mariham Y AbrahamGregory H Robinson
Journal of the American Chemical Society
Yuzhong WangGregory H Robinson
Journal of the American Chemical Society
Philipp BissingerKatharina Wagner
Journal of the American Chemical Society
Sudipta RoyHerbert W Roesky
© 2022 Meta ULC. All rights reserved