In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 75, No. 9 ( 2010), p. 931-947
Abstract:
Iodination of [ closo -1-CB 7 H 8 ] – (anion 1 ) with elemental iodine under various controlled conditions yields a continuum from mono- to hexaiodinated derivatives including the previously unknown [ closo -1-CB7H 5 -6,7,8-I 3 ] – (anion 5 ) and [ closo -1-CB7H 2 -2,3,4,6,7,8-I 6 ] – (anion 8 ). These species, characterized by mass spectrometry and NMR spectroscopy, and, in the case of 8 , by single-crystal X-ray diffraction, provide insight into the fluxional molecular behavior of anion 1 in solution. Investigation of direct electrophilic substitution on the carbon-vertex of anion 1 using standard conditions and reagents (deprotonation by BuLi followed by addition of electrophile) proved futile, but the same conditions when using the new triiodo-deravitive anion 5 resulted in the formation of the first eight-vertex C-methylated carborane anion [1-CH3- closo -1-CB 7 H 4 -6,7,8-I 3 ] – (anion 9 ), in 60% yield.
Type of Medium:
Online Resource
ISSN:
1212-6950
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
2010
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