We have located links that may give you full text access.
Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO.
Chemistry : a European Journal 2018 November 9
Four new acyclic diaminocarbenes (ADACs), viz. [(cyclo-CnH2n - 1)2N]2C (n = 5 - 7) and iPr2N-C-N(cyclo-C6H11)2, were synthesised by reacting the corresponding formamidinium hexafluorophosphates with NaN(SiMe3)2. Their nucleophilicities and electrophilicities were respectively judged from the 1JCH values determined for the N2CH unit of the corresponding formamidinium cations and from the 77Se NMR chemical shifts of the selenourea derivatives obtained from the reaction of elemental selenium with the corresponding ADACs. An ambiphilic profile essentially identical to that of the "Alder carbene" (iPr2N)2C was found in each case. Similar to the latter carbene, the new ADACs undergo a well-defined thermal decomposition by β-fragmentation, affording an alkene and a formamidine. The stabilities of [(cyclo-CnH2n - 1)2N]2C depend strongly on the value of n, following the order 6 > 5 > 7, with the latter congener being too unstable for isolation. [(cyclo-C6H11)2N]2C shows no thermal decomposition at room temperature in solution and is thus significantly more stable than (iPr2N)2C. The stability of iPr2N-C-N(cyclo-C6H11)2 is intermediate between that of (iPr2N)2C and [(cyclo-C6H11)2N]2C, its β-fragmentation selectively affording propene and iPrN=CH-N(cyclo-C6H11)2. [(cyclo-CnH2n - 1)2N]2C (n = 5 - 7) react readily with CO under mild conditions, selectively affording trisubstituted spirocyclic β-lactam derivatives with an antimicrobial activity spectrum similar to that of penicillin G.
Full text links
Related Resources
Trending Papers
Heart failure with preserved ejection fraction: diagnosis, risk assessment, and treatment.Clinical Research in Cardiology : Official Journal of the German Cardiac Society 2024 April 12
Proximal versus distal diuretics in congestive heart failure.Nephrology, Dialysis, Transplantation 2024 Februrary 30
Efficacy and safety of pharmacotherapy in chronic insomnia: A review of clinical guidelines and case reports.Mental Health Clinician 2023 October
World Health Organization and International Consensus Classification of eosinophilic disorders: 2024 update on diagnosis, risk stratification, and management.American Journal of Hematology 2024 March 30
Get seemless 1-tap access through your institution/university
For the best experience, use the Read mobile app
All material on this website is protected by copyright, Copyright © 1994-2024 by WebMD LLC.
This website also contains material copyrighted by 3rd parties.
By using this service, you agree to our terms of use and privacy policy.
Your Privacy Choices
You can now claim free CME credits for this literature searchClaim now
Get seemless 1-tap access through your institution/university
For the best experience, use the Read mobile app