Structural Reassignment of the Mono- and Bis-Addition Products from the Addition Reactions of <i>N</i>-(Diphenylmethylene)glycinate Esters to [60]Fullerene under Bingel Conditions
作者:Graham E. Ball、Glenn A. Burley、Leila Chaker、Bill C. Hawkins、James R. Williams、Paul A. Keller、Stephen G. Pyne
DOI:10.1021/jo051282u
日期:2005.10.1
esters (Ph2CNCH2CO2R) to [60]fullerene under Bingel conditions gives [60]fullerenyldihydropyrroles and not methano[60]fullerenyl iminoesters [C60C(CO2R)(NCPh2)] as previously reported. Unequivocal evidence for the structure of C60C(CO2Et)(NCPh2) was provided by INADEQUATE NMR studies on 13C enriched material. New mechanistic details are proposed to account for the formation of [60]fullerenyldihydropyrroles
Unexpected regiochemistry of a tethered bismethano[60]fullerene
作者:Glenn A. Burley、Paul A. Keller、Stephen G. Pyne、Graham E. Ball
DOI:10.1039/b005157h
日期:——
The structure of a novel tethered fullerenebis-adduct, of unexpected regiochemistry, has been unequivocally assigned using INADEQUATE 2D NMR experiments.
Synthesis and Characterization of Mono- and Bis-methano[60]fullerenyl Amino Acid Derivatives and Their Reductive Ring-Opening Retro-Bingel Reactions
作者:Glenn A. Burley、Paul A. Keller、Stephen G. Pyne、Graham E. Ball
DOI:10.1021/jo025928j
日期:2002.11.1
lycinate esters (Ph2C=NCH2CO2R) 3-6 to [60]fullerene under Bingel conditions gives, respectively, the methano[60]fullerenyl iminoesters 7-10. Upon treatment of 7-9 with sodium cyanoborohydride, in the presence of a protic or a Lewis acid, a novel reductive ring-opening reaction occurred to give the corresponding 1,2-dihydro[60]fullerenyl glycine derivatives 11-13. Using tethered bis-N-(diphenylmethylene)glycinate
Synthesis of Mono and Bis[60]fullerene-Based Dicationic Peptoids
作者:Sreenu Jennepalli、Katherine A. Hammer、Thomas V. Riley、Stephen G. Pyne、Paul A. Keller
DOI:10.1002/ejoc.201403046
日期:2015.1
us to synthesise [60]fullerenyldihydropyrrole peptides, prepared from the coupling of mono- and bis[60]fullerenyldihydropyrrolecarboxylic acids 4, 5 and 41 with presynthesised peptides 13, 16, 24, 28, 29 and 46. The resulting hydrophobic scaffolded di- and tetra-cationic derivatives were tested against Staphylococcus aureus NCTC 6571 and Escherichia coli NCTC 10418. The synthesis, characterisation