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


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Publication details

All authors or editorsPuerta Lombardi, Braulio M.; Pezoulas, Ethan R.; Suvinen, Roope A.; Harrison, Alexander; Dubrawski, Zachary S.; Gelfand, Benjamin S.; Tuononen, Heikki M.; Roesler, Roland

Journal or seriesChemical Communications

ISSN1359-7345

eISSN1364-548X

Publication year2022

Volume58

Issue number45

Pages range6482-6485

PublisherRoyal Society of Chemistry (RSC)

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/d2cc01476a

Publication open accessOpenly available

Publication channel open accessPartially 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.


Keywordsisomerismchemical compounds


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Ministry reportingYes

Reporting Year2022

JUFO rating2


Last updated on 2024-14-06 at 23:26