A practical synthesis of isomerically pure 1,10-difunctionalized derivatives of the [closo-1-CB9H10] anion.

Content Provider	Semantic Scholar
Author	Ringstrand, Bryan Baliński, Andrzej Franken, Andreas Kaszyński, Piotr
Copyright Year	2005
Abstract	The isomer-free [closo-1-CB9H(8)-1-COOH-10-I]- anion was prepared in four steps and 10% overall yield from B10H14. The key step is the skeletal isomerization of the [closo-2-CB9H8-2-COOH-7-I]- anion to a mixture of the 10- and 6-iodo derivatives of [closo-1-CB9H(9)-1-COOH]- formed in up to a 3:1 ratio. The carboxylic acid 4 was converted to the amine [closo-1-CB9H(8)-1-NH(2)-10-I]- using the Curtius reaction. The relative thermodynamic stability of each product was calculated at the DFT and MP2 levels of theory. The regioselectivity of electrophilic substitution in [closo-CB9H10]- derivatives was briefly investigated using the NBO population analysis of the MP2 wave function.
File Format	PDF HTM / HTML
DOI	10.1021/ic051311j
PubMed reference number	16323945
Journal	Medline
Volume Number	44
Issue Number	25
Alternate Webpage(s)	https://www.vanderbilt.edu/AnS/Chemistry/omrg/Articles/IC_2005_9561.pdf
Alternate Webpage(s)	https://doi.org/10.1021/ic051311j
Journal	Inorganic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article