Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates.
Nucleophilic cycloaddition of thiocyanates 1a-e with C60 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded C60-fused 2-iminotetrahydrothiophene derivatives 2a-e and methanofullerenes 3a-d. The product distributions were highly sensitive to the substrates employed. The 2-iminotetrahydrothiophene derivatives 2a-e could be further manipulated by hydrolysis and acetylation to give 2-oxotetrahydrothiophene derivatives 4a-e and 2-acetamidotetrahydrothiophene derivatives 5a-e. A possible reaction mechanism for the formation of products 2a-e and 3a-d was proposed.
Wang
Guan-Wu
GW
Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China. gwang@ustc.edu.cn
Li
Jia-Xing
JX
Xu
Yu
Y
D003500:Cyclization; D037741:Fullerenes / Q000737:chemistry*; D015394:Molecular Structure; D013861:Thiocyanates / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
D037741:Fullerenes; D013861:Thiocyanates; D013876:Thiophenes; C121030:tetrahydrothiophene; C069837:fullerene C60