Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

Guan-Wu Wang; Jia-Xing Li; Yu Xu

doi:10.1039/B807394E

Synthesis of C₆₀-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

Guan-Wu Wang,*^a^b Jia-Xing Li^a and Yu Xu^a

* Corresponding authors

^a Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, P. R. China
E-mail: gwang@ustc.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P. R. China

Abstract

Nucleophilic cycloaddition of thiocyanates 1a–e with C₆₀ in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded C₆₀-fused 2-iminotetrahydrothiophene derivatives 2a–e and methanofullerenes 3a–d. The product distributions were highly sensitive to the substrates employed. The 2-iminotetrahydrothiophene derivatives 2a–e could be further manipulated by hydrolysis and acetylation to give 2-oxotetrahydrothiophene derivatives 4a–e and 2-acetamidotetrahydrothiophene derivatives 5a–e. A possible reaction mechanism for the formation of products 2a–e and 3a–d was proposed.

Supplementary files

Publication details

The article was received on 01 May 2008, accepted on 02 Jun 2008 and first published on 26 Jun 2008

Article type: Paper

DOI: 10.1039/B807394E

Citation: Org. Biomol. Chem., 2008,6, 2995-2999

Request permissions
Synthesis of C₆₀-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

G. Wang, J. Li and Y. Xu, Org. Biomol. Chem., 2008, 6, 2995
DOI: 10.1039/B807394E
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Organic & Biomolecular Chemistry

Synthesis of C₆₀-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

Abstract

Supplementary files

Publication details

Synthesis of C₆₀-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates

Search articles by author

Spotlight

Advertisements