103144-37-2Relevant academic research and scientific papers
Contrasting Reactivity of CS2 with Cyclic vs. Acyclic Amidines
Ang, M. Trisha C.,Phan, Lam,Alshamrani, Aliyah K.,Harjani, Jitendra R.,Wang, Ruiyao,Schatte, Gabriele,Mosey, Nicholas J.,Jessop, Philip G.
, p. 7334 - 7343 (2015/11/25)
The interaction between carbon dioxide (CO2) and amidines such as 1,8-diazabicyclo[5.4.0]undecane (DBU) has been extensively studied, but the reaction of isovalent CS2 with such bases has been largely ignored, apart from a single crystallography report. Acyclic acetamidines are cleaved by CS2 at room temperature to give an isothiocyanate and a thioacetamide. Because the pathway to that cleavage involves a rotation that is difficult for cyclic amidines, the reaction of CS2 with cyclic amidines produces an entirely different product: a cyclic carbamic carboxylic trithioanhydride structure. The path to that product involves sp3 C-H activation leading to the formation of a new C-C bond at a carbon α to the central carbon of the amidine group. Alkylation and ring-opening of the cyclic carbamic carboxylic trithioanhydride has also been demonstrated under ambient conditions.
