A1 Journal article (refereed)
Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC) (2022)
Puerta Lombardi, B. M., Pezoulas, E. R., Suvinen, R. A., Harrison, A., Dubrawski, Z. S., Gelfand, B. S., Tuononen, H. M., & Roesler, R. (2022). Bis[cyclic (alkyl)(amino)carbene] isomers : Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC). Chemical Communications, 58(45), 6482-6485. https://doi.org/10.1039/d2cc01476a
JYU authors or editors
Publication details
All authors or editors: Puerta Lombardi, Braulio M.; Pezoulas, Ethan R.; Suvinen, Roope A.; Harrison, Alexander; Dubrawski, Zachary S.; Gelfand, Benjamin S.; Tuononen, Heikki M.; Roesler, Roland
Journal or series: Chemical Communications
ISSN: 1359-7345
eISSN: 1364-548X
Publication year: 2022
Volume: 58
Issue number: 45
Pages range: 6482-6485
Publisher: Royal Society of Chemistry (RSC)
Publication country: United Kingdom
Publication language: English
DOI: https://doi.org/10.1039/d2cc01476a
Publication open access: Openly available
Publication channel open access: Partially open access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/81139
Abstract
Isomeric bis(aldiminium) salts with a 1,4-cyclohexylene framework were synthesized. The first isolable bis(CAAC) was prepared from the trans-stereoisomer and its ditopic ligand competency was proven by conversion to iridium(I) and rhodium(I) complexes. Upon deprotonation, the cis-isomer yielded an electron rich olefin via a classic, proton-catalyzed pathway. The C[double bond, length as m-dash]C bond formation from the desired cis-bis(CAAC) was shown to be thermodynamically very favorable and to involve a small activation barrier. Compounds that can be described as insertion products of the cis-bis(CAAC) into the E–H bonds of NH3, CH3CN and H2O were also identified.
Keywords: isomerism; chemical compounds
Contributing organizations
Related projects
- Small Molecule Activation by Main-Group Compounds
- Tuononen, Heikki
- European Commission
Ministry reporting: Yes
Reporting Year: 2022
JUFO rating: 2