Sequential Camouflage of the arachno-6,9-C2B8H14 Cage by Substituents

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388980%3A_____%2F16%3A00461947" target="_blank" >RIV/61388980:_____/16:00461947 - isvavai.cz</a>
Alternative codes found
RIV/00216275:25310/16:39901647
Result on the web
<a href="http://dx.doi.org/10.1021/acs.inorgchem.6b00964" target="_blank" >http://dx.doi.org/10.1021/acs.inorgchem.6b00964</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.inorgchem.6b00964" target="_blank" >10.1021/acs.inorgchem.6b00964</a>

Result language
angličtina
Original language name
Sequential Camouflage of the arachno-6,9-C2B8H14 Cage by Substituents
Original language description
Sequential methylation of arachno-6,9-C2B8H14 (1) led to a series of methyl derivatives and finally to the camouflaging of all boron positions by mixed persubstitution. Thus, deprotonation of 1 produced the [arachno-6,9-C2B8H13] anion (1(-)), the methylation of which with MeI in tetrahydrofuran proceeded on the open-face boron vertexes with the formation of 5-Me-arachno-6,9-C2B8H13 (2; yield 28%) and 5,8-Me-2-arachno-6,9-C2B8H12 (3; yield 36%). Observed in this reaction was also a side formation of 2-Me-closo-1,6-C2B8H9 (4; yield 6%).The electrophilic AlCl3-catalyzed CH3+ attack of the neutral 1 in neat MeI at ambient temperature afforded 1,3-Me-2-arachno-6,9-C2B8H12 (5), while a 76-h heating at 120 degrees C generated a mixture of the di- and triiodo derivatives 1,2,3,4,8,10-Me-6-5,7-I2-arachno-6,9-C2B8H6 (6) and 1,2,3,4,7-Me-5-5,7,10-I-3-arachno-6,9-C2B8H6 (7). On the other hand, a HOTf-catalyzed reaction between 1 and MeOTf at reflux resulted in the isolation of 2-TfO-1,3.4,5,7,8,10-Me7-arachno-6,9-C2B8H6 (8; Tf = CF3SO2; yield 65%). The compounds were characterized by multinuclear (B-11, H-1, C-13, and F-19) NMR spectroscopy, mass spectrometry, and elemental analysis, and the structures of compounds 1, 1(-), 5, and 6 were established by X-ray diffraction analysis.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CA - Inorganic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA16-01618S" target="_blank" >GA16-01618S: Ten-vertex dicarbaborane molecular assemblies via alkylation</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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