Polyhedral Monocarbaborane Chemistry. A Review of Recent Developments Among C-Aryl Monocarbaborane Systems

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Title:Polyhedral Monocarbaborane Chemistry. A Review of Recent Developments Among C-Aryl Monocarbaborane Systems
Creators:
Franken, Andreas
Kilner, Colin A.
Thornton-Pett, Mark
Kennedy, John D.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 7, pp. 869-912
Uncontrolled Keywords:Brellochs Reaction, Cluster-closure reactions, Rearrangements, Boranes, Carboranes, Monocarbaboranes, Arenes, Aldehydes

Abstract

The Brellochs Reactions, of <i>nido</i>-B<sub>10</sub>H<sub>14</sub> with aromatic aldehydes to give [6-Ar-<i>nido</i>-6-CB<sub>9</sub>H<sub>11</sub>]<sup>-</sup> anions in high yield, now permits excellent entries into <i>C</i>-aryl monocarbaborane chemistry, which is reviewed. From [6-Ar-<i>nido</i>-6-CB<sub>9</sub>H<sub>11</sub>]<sup>-</sup>, one-step cluster-closure, cluster-Aufbau, or cluster-dismantling reactions yield [1-Ph-closo-1-CB<sub>11</sub>H<sub>11</sub>]<sup>-</sup>, [7-Ph-<i>nido</i>-7-CB<sub>10</sub>H<sub>12</sub>]<sup>-</sup>, [1-Ph-<i>closo</i>-1-CB<sub>9</sub>H<sub>9</sub>]<sup>-</sup>, [2-Ph-<i>closo</i>-2-CB<sub>9</sub>H<sub>9</sub>]<sup>-</sup>, [4-<i>closo</i>-4-PhCB<sub>8</sub>H<sub>8</sub>]<sup>-</sup> and [6-Ph-<i>arachno</i>-6-CB<sub>8</sub>H<sub>13</sub>]. Second-step reactions involving these products yield [2-Ph-<i>closo</i>-2-CB<sub>10</sub>H<sub>10</sub>]<sup>-</sup>, [6-Ph-<i>nido</i>-6-CB<sub>8</sub>H<sub>11</sub>], [1-Ph-<i>closo</i>-1-CB<sub>7</sub>H<sub>7</sub>]<sup>-</sup> and [4-Ph-<i>closo</i>-4-CB<sub>8</sub>H<sub>8</sub>]<sup>-</sup>, as well as alternative routes to [1-Ph-<i>closo</i>-1-CB<sub>11</sub>H<sub>11</sub>]<sup>-</sup> and [1-Ph-<i>closo</i>-1-CB<sub>9</sub>H<sub>9</sub>]<sup>-</sup>. This readier access to this extensive suite of <i>C</i>-aryl monocarbaboranes permits a readier examination of their derivative chemistry. Monohalogenated and poly-halogenated species [1-Ph-<i>closo</i>-1-CB<sub>9</sub>H<sub>9-<i>n</sub></i>X<i><sub>n</sub></i>]<sup>-</sup> and [1-Ph-<i>closo</i>-1-CB<sub>11</sub>H<sub>11-<i>n</sub></i>X<i><sub>n</sub></i>]<sup>-</sup> have been formed as well as (SMe<sub>2</sub>)-substituted {CB<sub>11</sub>} and {CB<sub>10</sub>} systems. Coupling reactions with <i>para</i>-substituted [XC<sub>6</sub>H<sub>4</sub>CB<sub>11</sub>H<sub>10</sub>X]<sup>-</sup> systems give rod-like anions, and with poly-iodinated [PhCB<sub>11</sub>H<sub>5</sub>I<sub>6</sub>]<sup>-</sup> and [PhCB<sub>9</sub>H<sub>4</sub>I<sub>5</sub>]<sup>-</sup> give the globular [PhCB<sub>11</sub>H<sub>5</sub>Ar<sub>5</sub>I]<sup>-</sup> and [PhCB<sub>9</sub>H<sub>4</sub>Ar<sub>4</sub>I]<sup>-</sup> anions. Additional interesting species include [PhCB<sub>11</sub>H<sub>10</sub>CH=CHCH<sub>3</sub>]<sup>-</sup>, [PhCB<sub>11</sub>H<sub>10</sub>SMe(CH<sub>2</sub>)<sub>4</sub>OH]<sup>-</sup> and [PhCB<sub>9</sub>H<sub>8</sub>-6-OH]<sup>-</sup>. A review with 49 references. <p>

Title:Polyhedral Monocarbaborane Chemistry. A Review of Recent Developments Among C-Aryl Monocarbaborane Systems
Creators:
Franken, Andreas
Kilner, Colin A.
Thornton-Pett, Mark
Kennedy, John D.
Uncontrolled Keywords:Brellochs Reaction, Cluster-closure reactions, Rearrangements, Boranes, Carboranes, Monocarbaboranes, Arenes, Aldehydes
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:67
Number:7
Page Range:pp. 869-912
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020869UNSPECIFIED
ID Code:1962
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Franken, Andreas; Kilner, Colin A.; Thornton-Pett, Mark; Kennedy, John D. (2002) Polyhedral Monocarbaborane Chemistry. A Review of Recent Developments Among C-Aryl Monocarbaborane Systems. Collection of Czechoslovak Chemical Communications, 67 (7). pp. 869-912. ISSN 0010-0765

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