About: Synthesis, characterisation and some chemistry of C- and B-substituted carboxylic acids of cobalt bis(dicarbollide)     Goto   Sponge   NotDistinct   Permalink

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  • Low temperature reactions of lithiated cobalt bis(1,2-dicarbollide)(1-) (1(-)) in DME with carbon dioxide leads to the substitution of 1(-) at the C-atoms by carboxy function(s). This results in a good yield formation of monosubstituted and disubstituted products of formulations [(1-HOOC-1,2-C2B9H10)(1', 2'-C2B9H11)3,3'-Co)](-) (2(-)) and [(HOOC)(2)-(1,2-C2B9H10)(2)-3,3'-Co](-)(3a, b(-)), respectively. Indeed, the latter compound is in fact a mixture of two diastereoisomers, denoted here as 1,1'-anti (3a(-)) and 1,2'-syn-isomer (3b(-)), from which only the former major species (3a(-)) could be isolated in pure form. Considerations about stereochemistry of these species are supported by geometry optimizations and calculations of 11B NMR shifts at the GIAO-DFT level. In addition, three monocarboxylic acids with three different linear spacers between the carboxy groups and the cage are reported. The first one of the formula [(1-HOOC-CH2-1,2-C2B9H10)(1', 2'-C2B9H11)-3,3'-Co]-(5-) results in a lithiation followed by reaction with BrCH2COOEt and hydrolysis of the respective ethyl ester (4-). Another one with ethylene chain [(1-HOOC-(CH2) 2-1,2-C2B9H10)( 1', 2'-C2B9H11)-3,3'-Co]-(6-) was prepared by the oxidation of a hydroxypropyl derivative of the ion 1(-). The sole representative of B-substituted species of the formulation [8-(HOOC-CH2-O-1,2C(2)B(9)H(10))(1', 2'-C2B9H11)-3,3'-Co]-(7(-)) is prepared by alkylation of the known 8-hydroxy derivatives of the ion 1-by BrCH2COOEt and alkaline hydrolysis. A synthetic route to active nitrofenyl esters (8(-), 9(-) and 10(-)) is described here based on the respective acids 5(-) to 7(-). As verified, the nitrophenyl esters provide easy access to the formation of amidic bonds between the boron cage and organic primary amino functions.
  • Low temperature reactions of lithiated cobalt bis(1,2-dicarbollide)(1-) (1(-)) in DME with carbon dioxide leads to the substitution of 1(-) at the C-atoms by carboxy function(s). This results in a good yield formation of monosubstituted and disubstituted products of formulations [(1-HOOC-1,2-C2B9H10)(1', 2'-C2B9H11)3,3'-Co)](-) (2(-)) and [(HOOC)(2)-(1,2-C2B9H10)(2)-3,3'-Co](-)(3a, b(-)), respectively. Indeed, the latter compound is in fact a mixture of two diastereoisomers, denoted here as 1,1'-anti (3a(-)) and 1,2'-syn-isomer (3b(-)), from which only the former major species (3a(-)) could be isolated in pure form. Considerations about stereochemistry of these species are supported by geometry optimizations and calculations of 11B NMR shifts at the GIAO-DFT level. In addition, three monocarboxylic acids with three different linear spacers between the carboxy groups and the cage are reported. The first one of the formula [(1-HOOC-CH2-1,2-C2B9H10)(1', 2'-C2B9H11)-3,3'-Co]-(5-) results in a lithiation followed by reaction with BrCH2COOEt and hydrolysis of the respective ethyl ester (4-). Another one with ethylene chain [(1-HOOC-(CH2) 2-1,2-C2B9H10)( 1', 2'-C2B9H11)-3,3'-Co]-(6-) was prepared by the oxidation of a hydroxypropyl derivative of the ion 1(-). The sole representative of B-substituted species of the formulation [8-(HOOC-CH2-O-1,2C(2)B(9)H(10))(1', 2'-C2B9H11)-3,3'-Co]-(7(-)) is prepared by alkylation of the known 8-hydroxy derivatives of the ion 1-by BrCH2COOEt and alkaline hydrolysis. A synthetic route to active nitrofenyl esters (8(-), 9(-) and 10(-)) is described here based on the respective acids 5(-) to 7(-). As verified, the nitrophenyl esters provide easy access to the formation of amidic bonds between the boron cage and organic primary amino functions. (en)
Title
  • Synthesis, characterisation and some chemistry of C- and B-substituted carboxylic acids of cobalt bis(dicarbollide)
  • Synthesis, characterisation and some chemistry of C- and B-substituted carboxylic acids of cobalt bis(dicarbollide) (en)
skos:prefLabel
  • Synthesis, characterisation and some chemistry of C- and B-substituted carboxylic acids of cobalt bis(dicarbollide)
  • Synthesis, characterisation and some chemistry of C- and B-substituted carboxylic acids of cobalt bis(dicarbollide) (en)
skos:notation
  • RIV/61388980:_____/14:00428161!RIV15-AV0-61388980
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(IAAX00320901)
http://linked.open...iv/cisloPeriodika
  • 13
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http://linked.open...aciTvurceVysledku
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http://linked.open...iv/duvernostUdaju
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  • 49000
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  • RIV/61388980:_____/14:00428161
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • BORON-CLUSTER COMPOUNDS; EFFICIENT EXTRACTANTS; ACTINIDE EXTRACTIONS (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [115B969D6A34]
http://linked.open...i/riv/nazevZdroje
  • Dalton Transactions
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  • 43
http://linked.open...iv/tvurceVysledku
  • Grüner, Bohumír
  • Hnyk, Drahomír
  • Šícha, Václav
  • Nekvinda, Jan
http://linked.open...ain/vavai/riv/wos
  • 000332475300023
issn
  • 1477-9226
number of pages
http://bibframe.org/vocab/doi
  • 10.1039/c3dt52870g
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