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Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction
| Content Provider | Scilit |
|---|---|
| Author | Mąkosza, Mieczysław Bechcicka, Małgorzata Wojciechowski, Krzysztof |
| Copyright Year | 2020 |
| Description | Acetals of dimethyl phenyl- and heteroaryl-α-hydroxymethanephosphonates were deprotonated to generate carbanions, which enter the vicarious nucleophilic substitution (VNS) of hydrogen in aromatic nitro compounds to form 4-nitrobenzhydrylphosphonates and α-heteroaryl-4-nitrobenzylphosphonates. Similarly acetals of cyanohydrins of heteroaromatic aldehydes (furfural and 2-formylthiophene) react to form heteroaryl 4-nitroarylacetonitriles. The anion of the hemiacetal of acetaldehyde is an efficient leaving group in the base-induced β-elimination step – the crucial step in the VNS reaction. The reaction selectively occurred at the para-position to the nitro group. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707230.pdf |
| ISSN | 00397881 |
| e-ISSN | 1437210X |
| DOI | 10.1055/s-0040-1707230 |
| Journal | Synthesis |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2020-08-25 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synthesis Organic Chemistry Arylmethanephosphonates Arylacetonitriles Vicarious Nucleophilic Substitution |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
