Product formation in the Prato reaction on Sc3N@D5h-C80: preference for [5,6]-bonds, and not pyracylenic bonds

Sílvia Osuna; Antonio Rodríguez-Fortea; Josep M. Poblet; Miquel Solà; Marcel Swart

doi:10.1039/C2CC17210K

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Product formation in the Prato reaction on Sc₃N@D_5h-C₈₀: preference for [5,6]-bonds, and not pyracylenic bonds†

Sílvia Osuna,^a Antonio Rodríguez-Fortea,^b Josep M. Poblet,^b Miquel Solà*^c and Marcel Swart*^cd

Author affiliations

* Corresponding authors

^a Dept. of Chemistry and Biochemistry, UCLA, Los Angeles, USA

^b Dept. Química Física i Inorgànica, Universitat Rovira i Virgili, c/Marcel·lí Domingo s/n, 43007 Tarragona, Spain

^c Institut de Química Computacional and Dept. de Química, Universitat de Girona, Campus Montilivi, 17071 Girona, Spain
E-mail: miquel.sola@udg.edu, marcel.swart@udg.edu

^d ICREA, Pg. Lluís Companys 23, 08010 Barcelona, Spain

Abstract

We report here reaction energies and NMR data for the N-tritylpyrrolidino mono-adducts of Sc₃N@D_5h-C₈₀. The pyracylene adduct that was previously suggested to be important for the Prato reaction is ruled out both from energetic and NMR points of view.

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Article information

DOI: https://doi.org/10.1039/C2CC17210K
Article type: Communication
Submitted: 19 Nov 2011
Accepted: 12 Dec 2011
First published: 13 Dec 2011

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Chem. Commun., 2012,48, 2486-2488

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Product formation in the Prato reaction on Sc₃N@D_5h-C₈₀: preference for [5,6]-bonds, and not pyracylenic bonds

S. Osuna, A. Rodríguez-Fortea, J. M. Poblet, M. Solà and M. Swart, Chem. Commun., 2012, 48, 2486 DOI: 10.1039/C2CC17210K

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