Experimental and Theoretical DFT Study on Synthesis of Sterically Crowded 2, 3, 3, (4)5‐Tetrasubstituted‐4‐nitroisoxazolidines via 1, 3‐Dipolar Cycloaddition Reactions Between Ketonitrones and Conjugated Nitroalkenes. (7th August 2015)

• Record Type: Journal Article
• Authors: Jasiński, Radomir; Mróz, Kamila; Kącka, Agnieszka
• Is Part Of: Journal of heterocyclic chemistry. Volume 53:Number 5(2016:Sep.)
• Page Start: 1424
• Page End: 1429
• Publication Date: 2015-08-07
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2442
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : Abstract : 1, 3‐Dipolar cycloaddition reactions between ketonitrones (1a, 1b, 1c, 1d, 1e ) and β‐substituted nitroalkenes (2a, 2b, 2c, 2d ) proceed under mild conditions, with complete regioselectivity, and lead with high yields to sterically crowded 2, 3, 3, 5‐tetrasubstituted‐4‐nitroisoxazolidines (3a, 3b, 3c, 3d, 3e, 3f ). Reaction course may be interpreted on the basis of nature of local, nucleophile–electrophile interactions. Moreover, density functional theory (DFT) simulations of reaction paths suggest that these reactions should be considered as polar, "one‐step two‐stage"cycloadditions . Subsequently, it has been found that similar reactions between ketonitrones and α‐substituted nitroalkenes do not allow to obtain the expected 2, 3, 3, 4‐tetrasubstituted‐4‐nitroisoxazolidines.