Phenyl-Induced 3,1,11-Rearrangement in the Synthesis of Mixed Pyrrolyl/Dicarbollide Cobaltadicarbaboranes

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Title:Phenyl-Induced 3,1,11-Rearrangement in the Synthesis of Mixed Pyrrolyl/Dicarbollide Cobaltadicarbaboranes
Creators:
Bertran, Josep
Viñas, Clara
Gomez, Sílvia
Lamrani, Mouad
Teixidor, Francesc
Sillanpää, Reijo
Kivekäs, Raikko
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 8, pp. 1263-1272
Uncontrolled Keywords:Pyrrolide, Cobaltacarboranes, Carboranes

Abstract

Mixed pyrrolide cobaltadicarbollides have been prepared from the reaction involving potassium pyrrolide, anhydrous CoCl<sub>2</sub> and the [7,8-(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>-<i>nido</i>-7,8-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>]<sup>-</sup> anion in dimethoxyethane. An alternative and higher-yield route consists in the reaction between 1,2-(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>-<i>closo</i>-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10 </sub>and potassium pyrrolide in the presence of anhydrous CoCl<sub>2</sub>. As confirmed by the X-ray diffraction analysis of [3-(η<sup>5</sup>-NC<sub>4</sub>H<sub>4</sub>)-1,11-(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>-<i>closo</i>-3,1,11-CoC<sub>2</sub>B<sub>9</sub>H<sub>9</sub>], the phenyl rings were found to enhance the rearrangement of the metallacarborane cluster carbons to produce the 3,1,11-isomer instead of the expected 3,1,2-derivative. As suggested by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, the electron-withdrawing properties and steric requirements of the phenyl rings facilitate the rearrangement.

Title:Phenyl-Induced 3,1,11-Rearrangement in the Synthesis of Mixed Pyrrolyl/Dicarbollide Cobaltadicarbaboranes
Creators:
Bertran, Josep
Viñas, Clara
Gomez, Sílvia
Lamrani, Mouad
Teixidor, Francesc
Sillanpää, Reijo
Kivekäs, Raikko
Uncontrolled Keywords:Pyrrolide, Cobaltacarboranes, Carboranes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:8
Page Range:pp. 1263-1272
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971263UNSPECIFIED
ID Code:1205
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Bertran, Josep; Viñas, Clara; Gomez, Sílvia; Lamrani, Mouad; Teixidor, Francesc; Sillanpää, Reijo; Kivekäs, Raikko (1997) Phenyl-Induced 3,1,11-Rearrangement in the Synthesis of Mixed Pyrrolyl/Dicarbollide Cobaltadicarbaboranes. Collection of Czechoslovak Chemical Communications, 62 (8). pp. 1263-1272. ISSN 0010-0765

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