The mechanism of 1,3-dipolar cycloaddition between 1-[2-(acetylamino)phenylsulfonyl]-1,2-propadiene 1 and a series of N-(4-substituted)phenyl-C-methoxycarbonylnitrilimines 2 has been reinvestigated on the basis of DFT calculations and a quantitative formulation of the HSAB principle. Comparison of the new computational results with experimental findings led to the formulation of a mechanistic scheme involving both 1,3-prototropic and 1,3-arylsulfonyl shifts. The role of silver cation is also pointed out. (C) 2003 Elsevier Science Ltd. All rights reserved.
Assessment of mechanistic hypotheses of 1,3-dipolar cycloaddition of (arylsulfonyl)allene to nitrilimines by DFT reactivity indices / G. Molteni, A. Ponti. - In: TETRAHEDRON. - ISSN 0040-4020. - 59:28(2003), pp. 5225-5229.
Assessment of mechanistic hypotheses of 1,3-dipolar cycloaddition of (arylsulfonyl)allene to nitrilimines by DFT reactivity indices
G. Molteni;
2003
Abstract
The mechanism of 1,3-dipolar cycloaddition between 1-[2-(acetylamino)phenylsulfonyl]-1,2-propadiene 1 and a series of N-(4-substituted)phenyl-C-methoxycarbonylnitrilimines 2 has been reinvestigated on the basis of DFT calculations and a quantitative formulation of the HSAB principle. Comparison of the new computational results with experimental findings led to the formulation of a mechanistic scheme involving both 1,3-prototropic and 1,3-arylsulfonyl shifts. The role of silver cation is also pointed out. (C) 2003 Elsevier Science Ltd. All rights reserved.Pubblicazioni consigliate
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