Shanbhag, Pramod ; Nareddy, Pradeep R. ; Dadwal, Mamta ; Mobin, Shaikh M. ; Namboothiri, Irishi N. N. (2010) Rauhut–Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes Organic and Biomolecular Chemistry, 8 (21). p. 4867. ISSN 1477-0520
Full text not available from this repository.
Official URL: http://doi.org/10.1039/c0ob00062k
Related URL: http://dx.doi.org/10.1039/c0ob00062k
Abstract
Reaction of nitroalkenes or nitrodienes with methyl vinyl ketone (MVK) or acrylate in the presence of the imidazole-LiCl catalyst system provides Rauhut-Currier (vinylogous Morita-Baylis-Hillman) adducts in moderate yield. Under similar conditions (imidazole-hydroquinone), nitroalkenes and nitrodienes undergo self-dimerization to afford the Rauhut-Currier adducts in varying yields. An alternative self-dimerization-nitro group elimination pathway in the presence tricyclohexylphosphine was observed with heteroaromatic nitroalkenes. A synthetically useful one-pot two step transformation of Rauhut-Currier adducts of nitroalkenes with MVK to 2,3-disubstituted cyclopentenones is also described.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to The Royal Society of Chemistry. |
| ID Code: | 121575 |
| Deposited On: | 19 Jul 2021 10:15 |
| Last Modified: | 19 Jul 2021 10:15 |
Repository Staff Only: item control page
