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

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 th...

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Veröffentlicht in:Journal of organic chemistry 2015-04, Vol.80 (7), p.3566-3571
Hauptverfasser: Li, Zong-Jun, Li, Shu-Hui, Sun, Tao, Hou, Hui-Lei, Gao, Xiang
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container_issue 7
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container_title Journal of organic chemistry
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creator Li, Zong-Jun
Li, Shu-Hui
Sun, Tao
Hou, Hui-Lei
Gao, Xiang
description 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.
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title 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
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