Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)
Open Access
Abstract
A series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N+≡C–R triple bond of the propionitrilium derivative [8-EtC≡N-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)]. The reactions with primary amines result in the formation of mixtures of E and Z isomers of amidines, whereas the reactions with secondary amines lead selectively to the E-isomers. The crystal molecular structures of E-[8-EtC(NMe2)=HN-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)], E-[8-EtC(NEt2)=HN-3,3′-Co(1,2- C2B9H10)(1′,2′-C2B9H11)] and E-[8-EtC(NC5H10)=HN-3,3′-Co(1,2-C2B9H10)(1′,2′-C2B9H11)] were determined by single crystal X-ray diffraction.Keywords
Funding Information
- Russian Science Foundation (21-73-10199)
This publication has 104 references indexed in Scilit:
- Coupling of Azomethine Ylides with Nitrilium Derivatives of closo‐Decaborate Clusters: A Synthetic and Theoretical StudyChempluschem, 2012
- 1,3-Dipolar Cycloaddition of Nitrones to a Nitrile Functionality in closo-Decaborate Clusters: A Novel Reactivity Mode for the Borylated C≡N GroupOrganometallics, 2012
- Reactions of nucleophilic addition of primary amines to the nitrilium derivative of the closo-decaborate anion [2-B10H9(N≡CCH3)]−Russian Journal of Inorganic Chemistry, 2011
- 2-[(1-{[3-(dimethylazaniumyl)propyl]methylamino}ethylidene)azaniumyl]nonahydro-closo-decaborate dimethyl sulfoxide disolvateActa Crystallographica Section E Crystallographic Communications, 2011
- Charge Transfer via the Dative N−B Bond and Dihydrogen Contacts. Experimental and Theoretical Electron Density Studies of Four Deltahedral BoranesThe Journal of Physical Chemistry A, 2011
- Amidines in Organic Synthesis2009
- Boron(8) substituted nitrilium and ammonium derivatives, versatile cobalt bis(1,2-dicarbollide) building blocks for synthetic purposesDalton Transactions, 2008
- Addition of HO-nucleophiles to free and coordinated nitrilesRussian Chemical Reviews, 2005
- Activation of Acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal Structures of Iridium−Amidine, Imino−Ether, Amido, and Amide ComplexesOrganometallics, 2000
- Carborane analogues of cobalticinium ionChemical Communications (London), 1965