Efficient access to amides of the carborane carboxylic acid [1-(COOH)–CB(11)H(11)](−)

The preparation of the carborane acid chloride [1-(COCl)–CB(11)H(11)](−) from the carboxylic acid [1-(COOH)–CB(11)H(11)](−) is reported. This acid chloride exhibits remarkable inertness towards moisture and can be stored under ambient conditions for several months. Reaction with amines affords secon...

Descripción completa

Detalles Bibliográficos
Autores principales: Shen, Yunjun, Zheng, Kai, Dontha, Rakesh, Pan, Yani, Liu, Jiyong, Duttwyler, Simon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081092/
https://www.ncbi.nlm.nih.gov/pubmed/35539747
http://dx.doi.org/10.1039/c8ra03067g
Descripción
Sumario:The preparation of the carborane acid chloride [1-(COCl)–CB(11)H(11)](−) from the carboxylic acid [1-(COOH)–CB(11)H(11)](−) is reported. This acid chloride exhibits remarkable inertness towards moisture and can be stored under ambient conditions for several months. Reaction with amines affords secondary and tertiary carborane amides [1-(CONR(1)R(2))–CB(11)H(11)](−) in moderate to high yields under mild conditions. Two of the amide products were characterized by X-ray crystallography in addition to spectroscopic analysis. Preliminary studies show that the amides can be reduced to the corresponding amines and that the acid chloride has the potential to serve as a starting material for carborane ester formation.

Ejemplares similares