Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base
Convergent paired electrosynthesis of β-nitroalcohols using an undivided cell was successfully demonstrated by combining anodic generation of benzaldehydes from benzyl alcohols and cathodic formation of nitromethyl anion from nitromethane (CH3NO2) via an electrogenerated base (EGB). Linear sweep vol...
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| Format: | Article |
| Language: | English |
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The Electrochemical Society of Japan
2023-11-01
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| Series: | Electrochemistry |
| Subjects: | |
| Online Access: | https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67083/_html/-char/en |
| _version_ | 1797447941143658496 |
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| author | Haruka HOMMA Ruka HASEGAWA Tomohiro YOKOYAMA Toshiki TAJIMA |
| author_facet | Haruka HOMMA Ruka HASEGAWA Tomohiro YOKOYAMA Toshiki TAJIMA |
| author_sort | Haruka HOMMA |
| collection | DOAJ |
| description | Convergent paired electrosynthesis of β-nitroalcohols using an undivided cell was successfully demonstrated by combining anodic generation of benzaldehydes from benzyl alcohols and cathodic formation of nitromethyl anion from nitromethane (CH3NO2) via an electrogenerated base (EGB). Linear sweep voltammetry measurements in 0.1 M Bu4NBF4/CH3NO2 and 0.1 M Bu4PBF4/CH3NO2 (M = mol L−1), and the electrolysis in the absence of a substrate using a divided cell suggested that N-methylhydroxylamine (CH3NHOH) may be formed as an EGB. Paired electrolysis of various benzyl alcohols was carried out to provide the corresponding β-nitroalcohols in moderate yields except for p-nitrobenzyl alcohol. |
| first_indexed | 2024-03-09T14:03:11Z |
| format | Article |
| id | doaj.art-b5ea62ec5e734ae6992cf3dfece5ca31 |
| institution | Directory Open Access Journal |
| issn | 2186-2451 |
| language | English |
| last_indexed | 2024-03-09T14:03:11Z |
| publishDate | 2023-11-01 |
| publisher | The Electrochemical Society of Japan |
| record_format | Article |
| series | Electrochemistry |
| spelling | doaj.art-b5ea62ec5e734ae6992cf3dfece5ca312023-11-30T06:15:00ZengThe Electrochemical Society of JapanElectrochemistry2186-24512023-11-01911111200811200810.5796/electrochemistry.23-67083electrochemistryConvergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated BaseHaruka HOMMA0Ruka HASEGAWA1Tomohiro YOKOYAMA2Toshiki TAJIMA3https://orcid.org/0009-0000-8933-1225Department of Applied Chemistry, Shibaura Institute of TechnologyDepartment of Applied Chemistry, Shibaura Institute of TechnologyDepartment of Applied Chemistry, Shibaura Institute of TechnologyDepartment of Applied Chemistry, Shibaura Institute of TechnologyConvergent paired electrosynthesis of β-nitroalcohols using an undivided cell was successfully demonstrated by combining anodic generation of benzaldehydes from benzyl alcohols and cathodic formation of nitromethyl anion from nitromethane (CH3NO2) via an electrogenerated base (EGB). Linear sweep voltammetry measurements in 0.1 M Bu4NBF4/CH3NO2 and 0.1 M Bu4PBF4/CH3NO2 (M = mol L−1), and the electrolysis in the absence of a substrate using a divided cell suggested that N-methylhydroxylamine (CH3NHOH) may be formed as an EGB. Paired electrolysis of various benzyl alcohols was carried out to provide the corresponding β-nitroalcohols in moderate yields except for p-nitrobenzyl alcohol.https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67083/_html/-char/enpaired electrosynthesiselectrogenerated basehenry reactionβ-nitroalcohol |
| spellingShingle | Haruka HOMMA Ruka HASEGAWA Tomohiro YOKOYAMA Toshiki TAJIMA Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base Electrochemistry paired electrosynthesis electrogenerated base henry reaction β-nitroalcohol |
| title | Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base |
| title_full | Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base |
| title_fullStr | Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base |
| title_full_unstemmed | Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base |
| title_short | Convergent Paired Electrosynthesis of β-Nitroalcohols Combining Anodic Generation of Benzaldehydes and Cathodic Formation of Nitromethyl Anion via an Electrogenerated Base |
| title_sort | convergent paired electrosynthesis of β nitroalcohols combining anodic generation of benzaldehydes and cathodic formation of nitromethyl anion via an electrogenerated base |
| topic | paired electrosynthesis electrogenerated base henry reaction β-nitroalcohol |
| url | https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67083/_html/-char/en |
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