Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C6) and amino acid esters.
The reaction between glycine methyl ester and C60 can be effectively controlled by different iodo-reagents. Addition of DIB ((diacetoxyiodo)benzene) yields the 2,5-bismethoxycarbonyl pyrrolidino[60]fullerene under ultrasonic irradiation; whereas addition of DIB-iodine results in the N-methoxycarbonylmethyl aziridino[60]fullerene under ultrasonic irradiation. The reaction of sarcosine methyl ester with C60 is similar to that of glycine methyl ester under these two conditions. Addition of just iodine to a mixture of sarcosine methyl ester and C60 affords the tetra(amino)[60]fullerene epoxide C60(O)((Me)NCH2COOMe)4. Possible mechanisms are discussed.
Zhang
Xiang
X
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Gan
Liangbing
L
Huang
Shaohua
S
Shi
Yaru
Y
D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis*; D012521:Sarcosine / Q000031:analogs & derivatives / Q000737:chemistry
D000596:Amino Acids; D004952:Esters; D037741:Fullerenes; D011759:Pyrrolidines; D007455:Iodine; C069837:fullerene C60; D005998:Glycine; D012521:Sarcosine