Kinetics and regioselectivity in the Diels–Alder reaction of fulleroids vs. methanofullerene and C60

Naohiko Ikuma; Yasunori Susami; Takumi Oshima

doi:10.1039/B918005B

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Kinetics and regioselectivity in the Diels–Alder reaction of fulleroids vs.methanofullerene and C₆₀†

Naohiko Ikuma,^a Yasunori Susami^a and Takumi Oshima*^a

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, Japan
E-mail: oshima@chem.eng.osaka-u.ac.jp
Fax: +81 6 6879 4593

Abstract

Fulleroids, obtained from the 1,3-dipolar cycloaddition of fullerene with a diazoalkane, have a [5,6]-open methylene bridge and two highly twisted bridgehead double bonds. The [H,H]- and [H,CN]-substituted fulleroids were found to display significantly enhanced and regioselective Diels–Alder addition as compared with the [6,6] closed methanofullerene and C₆₀ with 2,3-dimethyl-1,3-butadiene, but reduced and nonregioselective addition with cyclopentadiene. NMR analysis of the 1 : 1 adduct and quantum calculations indicated that the high reactivity and the regioselective addition are due to π-orbital misalignment at the bridgehead double bond.

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Supplementary files

Experimental procedure, NMR spectrum of 1b and 1 : 1 adduct of 1b and 3b PDF (2614K)

Article information

DOI: https://doi.org/10.1039/B918005B
Article type: Paper
Submitted: 01 Sep 2009
Accepted: 10 Dec 2009
First published: 18 Jan 2010

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Org. Biomol. Chem., 2010,8, 1394-1398

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Kinetics and regioselectivity in the Diels–Alder reaction of fulleroids vs. methanofullerene and C₆₀

N. Ikuma, Y. Susami and T. Oshima, Org. Biomol. Chem., 2010, 8, 1394 DOI: 10.1039/B918005B

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Organic & Biomolecular Chemistry