1370557-22-4

Upstream product

• 1370557-20-2 C₂₄H₃₁ClN₂O 
• 1370557-21-3 1,3-bis(1,3,5-trimethylphenyl)-5,5-dimethyl-4-keto-tetrahydro-pyrimidinium chloride 
• 4300-97-4 3-Chloropivaloyl chloride 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 

Downstream Products

• 1370557-32-6 C₂₅H₃₀N₂OS₂ 
• 1370557-23-5 C₂₉H₃₉N₃O 
• 1370557-26-8 C₃₂H₃₇N₃O 
• 1370557-27-9 C₃₃H₃₉N₃O 
• 1442459-55-3 C₃₀H₃₅N₂OP 
• 1433993-53-3 C₉₆H₁₂₀N₈O₄P₈ 

Relevant academic research and scientific papers

Stable Singlet Carbenes as Organic Superbases

A simple experimental procedure for scaling carbene Br?nsted basicity is described. The results highlight the strong basicity of pyrazol-4-ylidenes, a type of mesoionic carbene, also named cyclic-bentallenes (CBA). They are more basic (pKaH >42.7 in acetonitrile) than the popular proazaphosphatrane Verkade bases, and even the Schwesinger phosphazene superbase P4(tBu). The basicity of these compounds can readily be tuned, and they are accessible in multigram quantities. These results open new avenues for carbon centered superbases.

Tuning the electronic properties of carbenes: A systematic comparison of neighboring amino versus amido groups

A related series of six-membered carbenes featuring adjoining amino and/or amido groups (i.e, a diaminocarbene, a monoamido-aminocarbene (3), and a a diamidocarbene (6)) were systematically compared using crystallographic, spectroscopic, electrochemical, and density functional theory methods. The solid-state structure of 3 was found to exhibit inequivalent nitrogen-carbon bond lengths (Ccarbene-Namide = 1.395(4) A vs C carbene-Namine = 1.323(4) A). Moreover, the C carbene-Namide distance was longer than that measured in the solid-state structure of 6 (1.371(3) A), while the C carbene-Namine distance was similar to that measured in the solid-state structure of a cyclic alkyl-aminocarbene (1.315(3) A). Iridium complexes of the aforementioned carbenes were also evaluated, and the collected data revealed that the introduction of carbonyl groups to the carbene-containing scaffold had a nearly linear, additive effect on the E 1/2 potential of the carbene-ligated iridium I/II redox couple (+165 mV per carbonyl added) as well as the Tolman electronic parameter value of the corresponding carbene-Ir(CO)2Cl complex (ca. 7 cm-1 per carbonyl added). Beyond attenuated ligand donicity, the introduction of carbonyl groups was found to broaden the chemical reactivity: unlike prototypical N-heterocyclic carbenes, including diaminocarbenes, the monoamido-aminocarbene was found to couple to isonitriles to form the respective ketenimines.