Mechanism and regioselectivity of the 1,3-dipolar cycloaddition of methyleneamine N-oxide with cyclopent-3-ene-1,2-dione and its aza, oxa and thia analogues: a DFT approach

作者：Emamian Saeed Reza^*; Zahedi Ehsan

来源：Progress in Reaction Kinetics and Mechanism, 2012, 37(1): 90-102.

DOI：10.3184/146867812X13242290723237

• 1,3-dipolar cycloaddition
• nitrone
• regioselectivity
• density functional theory
• based reactivity indices
• FMO analysis

A theoretical study on the regioselectivity of 1,3-dipolar cycloaddition reactions between methyleneamine N-oxide (nitrone) and cyclopent-3-ene-1,2-dione (DPh1), pyrrole-2,3-dione (DPh2), furan-2,3-dione (DPh3) and thiophene-2,3-dione (DPh4) has been carried out by means of several theoretical approaches, namely, activation energies, Houk's rule based on FMO theory and DFT reactivity indices. The calculations were performed at the DFT-B3LYP/6-31G(d) level of theory using Gaussian 03. The present analysis shows that these reactions have an NED character. Moreover, the results obtained from energetic and electronic approaches, with the exception of Gazquez-Mendez rule based on NPA analysis, confirm that 1,5-regioisomer is the major product.

• 出版日期2012