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.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Xiang
X
Zhang
Liangbing
L
Gan
Shaohua
S
Huang
Yaru
Y
Shi
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