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The reaction of 1 with 2b afforded, in addition to the expected compound 3b in 25% yield, a minor compound 4 (8% yield), which was identified as the parent unsubstituted pyrrolidino[3,4:1,2][60]fullerene. The formation of this compound in which the aryl group on the pyrrolidine ring has been lost is not clear yet. However, some related cases have been reported in the literature. See: (a) Zhou, D.; Tan, H.; Luo, C.; Gan, L.; Huang, C.; Pan, J.; Lu, M.; Wu, Y. Tetrahedron Lett. 1995, 36, 9169-9172.
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Although the presence of two electron-releasing methoxy groups in the benzene ring could have an impact on the acidic character of the OH group, their relative meta position prevents the conjugative effect. A weak inductive effect cannot be, however, ruled out
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We want to thank to one of the referees for this interesting suggestion, which has allowed a better understanding of this cyclization process
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We want to thank to one of the referees for this interesting suggestion, which has allowed a better understanding of this cyclization process.
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