Communication

Construction of Fullerocyclobutene Derivatives through Copper(I)-Mediated Radical Annulation of C60Cl6 with Aryl Acetylenes

  1. Shuai Wang1,
  2. Ping Yan1,
  3. Hui-Ying Huang2,
  4. Prof. Zhuang-Ping Zhan1,
  5. Prof. Su-Yuan Xie1,*,
  6. Prof. Rong-Bin Huang1,
  7. Prof. Lan-Sun Zheng1

Article first published online: 22 AUG 2012

DOI: 10.1002/asia.201200494

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 7, Issue 11, pages 2531–2533, November 2012

Additional Information

How to Cite

Wang, S., Yan, P., Huang, H.-Y., Zhan, Z.-P., Xie, S.-Y., Huang, R.-B. and Zheng, L.-S. (2012), Construction of Fullerocyclobutene Derivatives through Copper(I)-Mediated Radical Annulation of C60Cl6 with Aryl Acetylenes. Chem. Asian J., 7: 2531–2533. doi: 10.1002/asia.201200494

Author Information

  1. 1

    State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005 (China), Fax: (+86) 592-2183047

  2. 2

    School of Life Science, Xiamen University, Xiamen 361005 (China)

*State Key Laboratory for Physical Chemistry of Solid Surfaces and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005 (China), Fax: (+86) 592-2183047

Publication History

  1. Issue published online: 10 OCT 2012
  2. Article first published online: 22 AUG 2012
  3. Manuscript Received: 3 JUN 2012

Funded by

  • National Basic Research 973 Program of China. Grant Number: 2011CB935901
  • National Nature Science Foundation of China. Grant Numbers: 21031004, 21021061

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Keywords:

  • cycloaddition;
  • copper;
  • fullerenes;
  • homogeneous catalysis;
  • radicals
Thumbnail image of graphical abstract

Have a radical ball! Reaction of C60Cl6 with aryl acetylenes through a copper(I)-mediated annulation route to form fullerocyclobutene derivatives is reported. The fullerocyclobutenes are obtained in 36–53 % yields and a possible radical mechanism is proposed for this novel reaction.

Featured Compounds

Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound A
Molecular Weight:933.36
Molecular Formula:C60Cl6
InChIKey:GJYRZQVMRNFBIH-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:923.707
Molecular Formula:C69H8Cl2O
InChIKey:ZVZDQDWWZCSRRO-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:963.814
Molecular Formula:C73H16Cl2
InChIKey:KZTIHWDXNZYAQM-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:893.681
Molecular Formula:C68H6Cl2
InChIKey:AEXZKIKDBDAUFR-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:972.577
Molecular Formula:C68H5BrCl2
InChIKey:RZJLQAPZZOJOBT-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:Not Available
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Compound 1b
Molecular Weight:172.2661
Molecular Formula:C13H16
InChIKey:APGNXGIUUTWIRE-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:102.1332
Molecular Formula:C8H6
InChIKey:UEXCJVNBTNXOEH-UHFFFAOYSA-N
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Compound 1d
Molecular Weight:181.029
Molecular Formula:C8H5Br
InChIKey:Not Available
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Compound 1e
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:ZVWWYEHVIRMJIE-UHFFFAOYSA-N
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Compound 1f
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:JRXXLCKWQFKACW-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2e
Molecular Weight:949.788
Molecular Formula:C72H14Cl2
InChIKey:SQVHHFLCWYVRTP-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:969.777
Molecular Formula:C74H10Cl2
InChIKey:ABCJSJGMRZXZOB-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:852.8012
Molecular Formula:C69H8O
InChIKey:OTXQLZKWMIGZCE-UHFFFAOYSA-N
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Compound E
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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