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Title: Electrochemical Oxidation of [1-X-12-I-CB 11 Me 10 – ] Anions: Formation of Borenium Ylides [12-Dehydro-1-X-CB 11 Me 10 ] and Iodonium Ylide Anions [{12-(1-X-CB 11 Me 10 – )} 2 I + ]
Award ID(s):
1566435
NSF-PAR ID:
10026033
Author(s) / Creator(s):
; ; ; ; ; ;
Date Published:
Journal Name:
Inorganic Chemistry
Volume:
55
Issue:
24
ISSN:
0020-1669
Page Range / eLocation ID:
12815 to 12821
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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  1. Abstract

    C(1)‐vinylation of [closo‐1‐CB9H10](A) and [closo‐1‐CB11H12](B) with 4‐benzyloxystyryl iodide followed by hydrogenation of the double bond and reductive deprotection of the phenol functionality led to C(1)‐(4‐hydroxyphenethyl) derivatives. The phenol functionality was protected as the acetate. The esters were then treated with PhI(OAc)2and the resulting isomers were separated kinetically (for derivatives of anionA) or by chromatography (for derivatives of anionB) giving the difunctionalized building blocks in overall yields of 9 % and 50 %, respectively. A similar series of reactions was performed starting with anionsAandBand 4‐methoxystyryl bromide and iodide. Significant differences in the reactivity of derivatives of the two carborane anions were rationalized with DFT computational results. Application of the difunctionalized carboranes as building blocks was demonstrated through preparation of two ionic liquid crystals. The extensive synthetic work is accompanied by single crystal XRD analysis of six derivatives.

     
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