Contrasting Reactivity of CS2with Cyclic vs. Acyclic Amidines

Autor:	Ruiyao Wang, M. Trisha C. Ang, Aliyah K. Alshamrani, Philip G. Jessop, Gabriele Schatte, Nicholas J. Mosey, Jitendra R. Harjani, Lam Phan
Rok vydání:	2015
Předmět:	Carbon disulfide Chemistry Organic Chemistry chemistry.chemical_element Alkylation Cleavage (embryo) Medicinal chemistry Amidine chemistry.chemical_compound Isothiocyanate Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Undecane Carbon
Zdroj:	European Journal of Organic Chemistry. 2015:7334-7343
ISSN:	1434-193X
DOI:	10.1002/ejoc.201500973
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7a8a0641c461d0ab1a3c438058441784 https://doi.org/10.1002/ejoc.201500973 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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