Benzylamine imines as versatile precursors to azomethine and nitrile ylides in the [2 + 3] cycloaddition reactions with [60]fullerene

Synthesis and Functionalization of Symmetrical 2,5-Diaryl Fulleropyrrolidines: Ferric Perchlorate-Mediated One-Step Reaction of [60]Fullerene with Arylmethanamines

“…All high-resolution mass spectra of these new products gave the correct [M + H] + peaks along with the signals at about 720 arising from the loss of the addends. Their UV–vis spectra resemble those of other fulleropyrrolidine derivatives − and showed a peak at 431–434 nm, which is a characteristic absorption for the 1,2-adduct of C 60 . Their IR spectra displayed the absorptions at 3309–3330 cm –1 , corresponding to the stretching vibrations of the NH group.…”

“…Pioneering work on fulleropyrrolidine derivatives was conducted by Prato and co-workers through the reaction of [60]­fullerene (C 60 ) with azomethine ylides generated in situ by decarboxylation of immonium salts derived from condensation of α-amino acids with aldehydes/ketones (Prato reaction) . Fulleropyrrolidines could also be synthesized through several alternative methods such as thermal ring opening of aziridines, , thermal loss of CO 2 from oxazolidinones, , acid-catalyzed or thermal desilylation of trimethylsilyl amino derivatives, tautomerization of imines, reaction with aldehydes in the presence of aqueous ammonia, picolylamines, and dibenzylamine, thermal reaction of α-amino acids and amino acid esters, or reaction of halides and amino acids . Photochemical treatment of tertiary amines, α-amino acid esters, , or aminopolycarboxylic esters with C 60 was also applied to prepare pyrrolidine derivatives.…”

New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems

“…Apparently, pyrrolinofullerene 33c´ has been synthesized in the earlier study 55 as well; however, structure 33c″ has been erroneously assigned to the reac tion product because of the low quality of the 13 C NMR spectrum. Earlier, 48 we have also misinterpreted the spec troscopic data for a mixture of compounds 33c´ and 32c. We assigned the structure of pyrrolinofullerene 33c″´ con taining two nitrophenyl group to the reaction product because some signals in the 1 H NMR spectrum were acci dentally identical.…”

“…In the further study, we examined the possibility of generation of ylides from imines con taining no electron withdrawing groups that stabilize the carbanionic center, as in benzylamine based imine 31a (Scheme 23). 48 The reaction of imine 31a, C 60 , and butyric acid (8 equiv.) in 1,2 DCB under reflux in an argon atmo sphere for 10-15 h leads to pyrrolidinofullerene 32a and pyrrolinofullerene 33a with ~50% conversion of fullerene.…”

Study The Effect of Factors on the Rate Constant (K) for Some Substituted Benzyl-amine Using Theoretical Calculations

“…Benzyl-amine used as a reagent to prepare compounds like Pyrrolidino. The voltammetric instrumental (cyclic voltammetry) was been used to measure and characterized the reactions [10].…”