Exploration for Regioselective fullerene derivatives via of synthetic intermediates fulleroid/azafulleroid having high reactive anti-Bredt double bonds

KAKEN

About This Project

Japan Grant Number
JP24750039 (JGN)
Funding Program
Grants-in-Aid for Scientific Research
Funding Organization
Japan Society for the Promotion of Science

Kakenhi Information

Project/Area Number
24750039
Research Category
Grant-in-Aid for Young Scientists (B)
Allocation Type
  • Multi-year Fund
Review Section / Research Field
  • Science and Engineering > Chemistry > Basic chemistry > Organic chemistry
Research Institution
  • Osaka University
Project Period (FY)
2012-04-01 〜 2014-03-31
Project Status
Completed
Budget Amount*help
4,550,000 Yen (Direct Cost: 3,500,000 Yen Indirect Cost: 1,050,000 Yen)

Research Abstract

Electrophilic/acidic/nucleophilic additions to fulleroid/azafulleroid with anti-Bredt double bonds were investigated to evaluate their regioselectivity and discover novel reactions. Electrophilic oxidant mCPBA reacted with fulleroid to give hydroxyester products while oxidation with C60 gave epoxides. On the other hand, the oxidation with azafulleroid preferentially lead to the oxidation of nitrogen bridge, followed by oxidative deamination to give pristine C60. Acid catalytic arylation of azafulleroids lead to monoarylated/pentakisarylated products, depended on the ambident basicity of anti-Bredt enamine moiety of azafulleroids. Moreover, nucleophilic addition of Grignard reagents with azafulleroid gave highly regioselective adduct due to the nitrogen coordination with the magnesium.

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