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高效获取碳硼烷羧酸[1-(COOH)-CBH]的酰胺。

Efficient access to amides of the carborane carboxylic acid [1-(COOH)-CBH].

作者信息

Shen Yunjun, Zheng Kai, Dontha Rakesh, Pan Yani, Liu Jiyong, Duttwyler Simon

机构信息

Department of Chemistry, Zhejiang University Zheda Road 38 310027 Hangzhou P.R. China

出版信息

RSC Adv. 2018 Jun 19;8(40):22447-22451. doi: 10.1039/c8ra03067g.

DOI:10.1039/c8ra03067g
PMID:35539747
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9081092/
Abstract

The preparation of the carborane acid chloride [1-(COCl)-CBH] from the carboxylic acid [1-(COOH)-CBH] 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-(CONRR)-CBH] 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.

摘要

报道了由羧酸[1-(COOH)-CBH]制备碳硼烷酰氯[1-(COCl)-CBH]的方法。该酰氯对水分表现出显著的惰性,可在环境条件下储存数月。在温和条件下,与胺反应能以中等到高的产率得到仲碳硼烷酰胺和叔碳硼烷酰胺[1-(CONRR)-CBH]。除光谱分析外,其中两种酰胺产物还通过X射线晶体学进行了表征。初步研究表明,酰胺可被还原为相应的胺,且该酰氯有潜力作为形成碳硼烷酯的起始原料。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c260/9081092/e06e12930918/c8ra03067g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c260/9081092/e76a4d723b02/c8ra03067g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c260/9081092/e06e12930918/c8ra03067g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c260/9081092/e76a4d723b02/c8ra03067g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c260/9081092/e06e12930918/c8ra03067g-f2.jpg

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