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Upstream product

• 110-52-1 1,4-dibromo-butane 
• 75105-48-5 N,N'-dimesitylformamidine 
• 88-05-1 2,4,6-trimethylaniline 

Relevant academic research and scientific papers

The p: K a values of N-aryl imidazolinium salts, their higher homologues, and formamidinium salts in dimethyl sulfoxide

A series of imidazolinium salts, their six-, seven- A nd eight-membered homologues, and the related formamidinium salts were prepared, and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each type of structural variation on the acidity of each salt was considered, particularly noting the importance of ring size and the effect of the steric and electronic nature of the N-aryl substituents. The effect of a cyclic structure was also probed through comparing the cyclic systems with the corresponding formamidinium salts, noting the importance of conformational flexibility in the latter cases. Along with allowing choice of appropriate bases for deprotonation of these species, it is anticipated that the data presented will aid in the understanding of the nucleophilicity, and potentially catalytic efficacy, of the corresponding carbenes.

Anionic ring-opening homo- and copolymerization of lactams by latent, protected N-heterocyclic carbenes for the preparation of PA 12 and PA 6/12

Laurolactam (LL) is polymerized in the bulk using strongly basic N-heterocyclic carbenes (NHCs) as initiators at temperatures of 180-200 C to prepare the corresponding polyamide (PA 12). In-situ rheology of the polymerization progress reveals that an anionic mechanism is active, which is supported by the strong dependence of initiator activity on the basicity of the NHCs. GPC data and kinetic investigations show the process to be moderately controlled and fast, allowing high or quantitative yields in short polymerization times. Fifteen different NHC-CO2-adducts and NHC-metal complexes were used as thermally labile but room temperature stable NHC-precursors. Depending on the ring size and N-substituent, some of these protected NHCs allow forming a mixture of monomer and NHC-precursor that is suitable for long-term storage and readily polymerizable by simple heating. All polymerizations are executed without activator or other additives and thus represent a true one-component system for the production of PA 12. Finally, LL is copolymerized with ε-caprolactam (ε-CLA). It is found that a copolymer with a considerable gradient is formed, with ε-CLA being incorporated preferentially at the onset of the polymerization.

Six- and seven-membered ring carbenes: Rational synthesis of amidinium salts, generation of carbenes, synthesis of Ag(I) and Cu(I) complexes

Reactions of neat 1,3- and 1,4-dibromides with N,N′-diarylformamidines in the presence of diisopropylethylamine (DIPEA) afford corresponding amidinium salts in high yields (>80%). Six- and seven-membered ring amidinium salts bearing bulky Mes (2,4,6-Mesu