Prato cycloaddition reaction

This is mainly due to their laborious purification procedures and their required chemical modification for solubilization. Only recently, Prato et al. reported the electrochemistry of carbon nanotubes functionalized using the 1,3-dipolar cycloaddition reaction.120 The cyclic voltammogram obtained is shown in Fig. 8.9. 

Semiempirical AMI and DFT (B3LYP/6-31G ) calculations were used to investigate the highly diastereoselective 1,3-dipolar cycloaddition of 1,4-dihydropyridine- (g) containing azomethine ylides to [60]fullerene (Prato s reaction). The activation energy for the four calculated transition state structures favours the formation of SSaS and... 

For the formation of 15 (Figure 6.9) a different mechanism has been proposed [62]. Reaction of singlet oxygen with the corresponding amine (iminodiacetic methylester) leads - after two H-abstractions - to an azomethine ylide as a key intermediate. This ylide can add to the double bond via a [3-i-2]-cycloaddition related to the Prato reaction (Section 4.3.4). 

Besides, Prato and coworkers have reported that CNTs underwent 1,3-dipoIar cycloaddition when heated in DMF in the presence of a-amino acid and aldehyde. This reaction provides a versatile and powerful approach to attach different functionalities to CNTs and these functional groups can be further coupled with amino acids and bioactive peptides. It has been demonstrated that some of the peptide-functionalized CNTs can enhance the immunization to virus-specific neutralizing antibody responses. ... 

Perfluorinated BSubPc bearing axial m-formylphenoxy group 196 [99] was used for preparation conjugates with fullerene (Scheme 51) as tunable molecular scaffolds for intramolecular electron and energy transfer processes [110]. The azome-thine ylide formed by treatment of the formyl derivative 196 with A -methylglycine gives the conjugate with fullerene 197 (44 %) in a dipolar 1,3-cycloaddition (Prato reaction). 

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