Reductive benzylation of singly bonded 1,2,4,15-C60 dimers with an oxazoline or imidazoline heterocycle: unexpected formation of 1,2,3,16-C60 adducts and insights into the reactivity of singly bonded C60 dimers.
Upon reduction, singly bonded 1,2,4,15-C60 dimers with an oxazoline or imidazoline heterocycle dissociate into monoanionic 1,2,4-C60 intermediates, which surprisingly leads to the formation of 1,2,3,16-C60 rather than 1,2,4,15-C60 adducts of the original configuration by further benzylation, even though the analogue of dibenzylated C60 oxazoline with a 1,2,4,15-configuration is stable and has been obtained. These results are corroborated by computational calculations, which rationalize the reaction and clarify the structure of the 1,2,3,16-C60 adducts, providing new insights into the intrinsic reactivity of singly bonded C60 dimers.
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Zong-Jun
ZJ
Li
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Shu-Hui
SH
Li
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Tao
T
Sun
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Hui-Lei
HL
Hou
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022, China.
Xiang
X
Gao