Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)
A series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N<sup>+</sup>≡C–R triple bond of the propionitrilium derivative [8-EtC≡N-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</su...
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6544 |
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| author | Ekaterina V. Bogdanova Marina Yu. Stogniy Kyrill Yu. Suponitsky Igor B. Sivaev Vladimir I. Bregadze |
| author_facet | Ekaterina V. Bogdanova Marina Yu. Stogniy Kyrill Yu. Suponitsky Igor B. Sivaev Vladimir I. Bregadze |
| author_sort | Ekaterina V. Bogdanova |
| collection | DOAJ |
| description | A series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N<sup>+</sup>≡C–R triple bond of the propionitrilium derivative [8-EtC≡N-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)]. The reactions with primary amines result in the formation of mixtures of <i>E</i> and <i>Z</i> isomers of amidines, whereas the reactions with secondary amines lead selectively to the <i>E</i>-isomers. The crystal molecular structures of <i>E</i>-[8-EtC(NMe<sub>2</sub>)=HN-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)], <i>E</i>-[8-EtC(NEt<sub>2</sub>)=HN-3,3′-Co(1,2- C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)] and <i>E</i>-[8-EtC(NC<sub>5</sub>H<sub>10</sub>)=HN-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)] were determined by single crystal X-ray diffraction. |
| first_indexed | 2024-03-10T05:55:44Z |
| format | Article |
| id | doaj.art-4446a89e599541dca77225f973a79b5b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:55:44Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4446a89e599541dca77225f973a79b5b2023-11-22T21:22:55ZengMDPI AGMolecules1420-30492021-10-012621654410.3390/molecules26216544Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)Ekaterina V. Bogdanova0Marina Yu. Stogniy1Kyrill Yu. Suponitsky2Igor B. Sivaev3Vladimir I. Bregadze4A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, RussiaA series of novel cobalt bis(dicarbollide) based amidines were synthesized by the nucleophilic addition of primary and secondary amines to highly activated B-N<sup>+</sup>≡C–R triple bond of the propionitrilium derivative [8-EtC≡N-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)]. The reactions with primary amines result in the formation of mixtures of <i>E</i> and <i>Z</i> isomers of amidines, whereas the reactions with secondary amines lead selectively to the <i>E</i>-isomers. The crystal molecular structures of <i>E</i>-[8-EtC(NMe<sub>2</sub>)=HN-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)], <i>E</i>-[8-EtC(NEt<sub>2</sub>)=HN-3,3′-Co(1,2- C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)] and <i>E</i>-[8-EtC(NC<sub>5</sub>H<sub>10</sub>)=HN-3,3′-Co(1,2-C<sub>2</sub>B<sub>9</sub>H<sub>10</sub>)(1′,2′-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub>)] were determined by single crystal X-ray diffraction.https://www.mdpi.com/1420-3049/26/21/6544cobalt bis(dicarbollide)nitrilium derivativesamidinesnucleophilic addition reactionssynthesisstructure |
| spellingShingle | Ekaterina V. Bogdanova Marina Yu. Stogniy Kyrill Yu. Suponitsky Igor B. Sivaev Vladimir I. Bregadze Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) Molecules cobalt bis(dicarbollide) nitrilium derivatives amidines nucleophilic addition reactions synthesis structure |
| title | Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) |
| title_full | Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) |
| title_fullStr | Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) |
| title_full_unstemmed | Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) |
| title_short | Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide) |
| title_sort | synthesis of boronated amidines by addition of amines to nitrilium derivative of cobalt bis dicarbollide |
| topic | cobalt bis(dicarbollide) nitrilium derivatives amidines nucleophilic addition reactions synthesis structure |
| url | https://www.mdpi.com/1420-3049/26/21/6544 |
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