SYNTHESIS OF MONOETHYL-O-CARBORANES, DIETHYL-O-CARBORANES, TRIETHYL-O-CARBORANES, AND TETRAETHYL-O-CARBORANES BY ELECTROPHILIC ALKYLATION OF O-CARBORANE WITH ETHYL-BROMIDE IN THE PRESENCE OF ALCL3 AND THEIR TRANSFORMATIONS

Citation
Li. Zakharkin et al., SYNTHESIS OF MONOETHYL-O-CARBORANES, DIETHYL-O-CARBORANES, TRIETHYL-O-CARBORANES, AND TETRAETHYL-O-CARBORANES BY ELECTROPHILIC ALKYLATION OF O-CARBORANE WITH ETHYL-BROMIDE IN THE PRESENCE OF ALCL3 AND THEIR TRANSFORMATIONS, Russian chemical bulletin, 45(11), 1996, pp. 2614-2622
Citations number
16
Categorie Soggetti
Chemistry
Journal title
ISSN journal
10665285
Volume
45
Issue
11
Year of publication
1996
Pages
2614 - 2622
Database
ISI
SICI code
1066-5285(1996)45:11<2614:SOMDT>2.0.ZU;2-Y
Abstract
Optimal conditions for the preparation of 9-ethyl-, 9,12-diethyl, 8,9, 12-triethyl-, and 8,9,10,12-tetraethyl-o-carboranes under the action o f EtBr on o-carborane in the presence of AlCl3 were determined. The be havior of these o-carborane derivatives towards electrophilic and nucl eophilic reagents was studied. The presence of four ethyl groups in po sitions 8, 9, 10, and 12 of the carborane polyhedron increases the ele ctron density on the boron atoms in positions 4, 5, 7, and 11 to the p oint where they are able to enter into reactions of electrophilic subs titution, and in positions 3 and 6 to the point that they become resis tant to the action of nucleophilic reagents. Reactions of 1,2-dilithiu m-8,9,10,12-tetraethyl-o-carborane with various electrophilic reagents were studied.