Issue 1, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Products from the reaction of C60F18 with sarcosine and aldehydes: the Prato reaction

Xian-wen Wei,a   Anthony G. Avent,a   Olga V. Boltalina,b   Joan M. Streetc  and  Roger Taylor*a  

* Corresponding authors

a The Chemistry Laboratory, CPES School, Sussex University, Brighton, UK

b Chemistry Department, Moscow State University, Moscow 119899, Russia

c Chemistry Department, The University, Southampton, UK

Abstract

Various pyrrolidinofullerenes (both mono- and bis-addition products) have been isolated from the reaction between toluene solutions of C60F18, N-methyl-2-aminoethanoic acid (sarcosine) and either formaldehyde or benzaldehyde. Both mono- and bis-addition products were obtained and either partially of fully characterised. The main mono-addition product from the reaction with formaldehyde was also obtained from reactions with the other aldehydes, indicating that formaldehyde may be present in sarcosine, or generated from it through in situ oxidation by the fullerene. The main mono-addition product from reaction of C60F18 with toluene solutions of sarcosine and benzaldehyde was obtained also in the absence of benzaldehyde. This anomaly was traced to the presence of benzaldehyde (0.05%) in HPLC grade toluene, which may be increased by oxidation of toluene during the reaction conditions.

Graphical abstract: Products from the reaction of C60F18 with sarcosine and aldehydes: the Prato reaction

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Article information

DOI
https://doi.org/10.1039/B106877F
Article type
Paper
Submitted
30 Jul 2001
Accepted
26 Oct 2001
First published
21 Nov 2001

J. Chem. Soc., Perkin Trans. 2, 2002, 47-52

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Products from the reaction of C60F18 with sarcosine and aldehydes: the Prato reaction

X. Wei, A. G. Avent, O. V. Boltalina, J. M. Street and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 2002, 47 DOI: 10.1039/B106877F

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