H-bond-assisted regioselective (cis-1) intramolecular nucleophilic addition of the hydroxyl group to [60]fullerene

The Journal of Organic Chemistry
Marta IzquierdoNazario Martín

Abstract

The one-step reaction of 2,6-dihydroxyphenylmethyl ketone and sarcosine with [60]fullerene in refluxing chlorobenzene affords, in a totally regioselective process, the cis-1 bicyclic-fused organofullerene through a new intramolecular nucleophilic addition of one hydroxy group to the fullerene double bond. Experimental findings reveal the presence of a methyl group on C-2 of the pyrrolidine ring as an essential requirement for the cyclization process, whereas the existence of a H-bond between a second hydroxylic group and the nitrogen atom of the pyrrolidine ring seems to favor the approaching geometry without determining the reaction outcome. Theoretical calculations using the two-layered ONIOM approach and density functional theory support the experimental findings, predicting the strong impact that the presence of the methyl substituent on the C-2 of the pyrrolidine ring has on the molecular geometry and, hence, on the intramolecular cyclization process.

References

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Citations

Oct 30, 2016·The Journal of Physical Chemistry. a·Cercis Morera-BoadoJosé M García de la Vega
Oct 18, 2013·Angewandte Chemie·Marta IzquierdoLuis Echegoyen
Nov 27, 2010·Physical Chemistry Chemical Physics : PCCP·Sílvia OsunaMiquel Solà
Oct 6, 2012·Organic & Biomolecular Chemistry·San-E ZhuShi-Jin Chu
Jun 26, 2021·Chemical Communications : Chem Comm·Wen-Qiang LuGuan-Wu Wang
Mar 29, 2011·The Journal of Physical Chemistry. a·Sílvia OsunaMiquel Solà
Apr 9, 2015·Chemical Reviews·Lung Wa ChungKeiji Morokuma
Apr 23, 2019·The Journal of Organic Chemistry·Yutaka MatsuoYong Wan Jin

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