Phosphonylpyrazoles from Bestmann−Ohira Reagent and Nitroalkenes: Synthesis and Dynamic NMR Studies

Muruganantham, Rajendran ; Namboothiri, Irishi (2010) Phosphonylpyrazoles from Bestmann−Ohira Reagent and Nitroalkenes: Synthesis and Dynamic NMR Studies Journal of Organic Chemistry, 75 (7). pp. 2197-2205. ISSN 0022-3263

Full text not available from this repository.

Official URL: http://doi.org/10.1021/jo902595e

Related URL: http://dx.doi.org/10.1021/jo902595e

Abstract

Application of diethyl 1-diazo-2-oxopropylphosphonate (Bestmann-Ohira reagent) as a cycloaddition partner with nitroalkenes has been extensively investigated. Base-mediated reaction of the Bestmann-Ohira reagent with various nitroalkenes such as β-substituted, αβ-disubstituted, and nitroethylene that are part of a carbocyclic or heterocyclic ring provided functionalized phosphonylpyrazoles through a one-pot regio selective reaction at room temperature in high yield. The substituted nitroalkenes employed in these reactions also included Morita-Baylis-Hillman adducts of conjugated nitroalkenes with various electrophiles. Detailed dynamic NMR studies were performed on the prototropic tautomerism exhibited by the phosphonylpyrazoles using CDCl 3 and DMSO-d6 as solvents and 1H and 31P as the probe nuclei. These studies unraveled the existence of two tautomers in solution with a small energy difference but considerable barrier to interconversion.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:121576
Deposited On:19 Jul 2021 10:17
Last Modified:19 Jul 2021 10:17

Repository Staff Only: item control page