Transition-metal-catalyzed synthesis of organophosphate-appended cyclobutanofullerenes from C60 and secondary propargylic phosphates

[Display omitted] •Secondary propargylic phosphates are used to functionalize fullerene.•Organophosphate-appended cyclobutanofullerenes were synthesized and characterized as major products.•Cyclobutenofullerenes were synthesized and characterized as minor products. In this study, we demonstrated the...

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Bibliographic Details
Published in:Tetrahedron letters 2023-01, Vol.115, p.154299, Article 154299
Main Authors: Yamada, Michio, Ueno, Yui, Uokawa, Yuta, Maeda, Yutaka
Format: Article
Language:English
Subjects:
Allenes
Cycloaddition
Cyclobutanofullerenes
Cyclobutenofullerenes
Propargylic phosphates
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Summary:[Display omitted] •Secondary propargylic phosphates are used to functionalize fullerene.•Organophosphate-appended cyclobutanofullerenes were synthesized and characterized as major products.•Cyclobutenofullerenes were synthesized and characterized as minor products. In this study, we demonstrated the synthesis and characterization of organophosphate-appended cyclobutanofullerenes in the presence of a transition-metal catalyst by reacting C60 with secondary propargylic phosphates. In the reactions demonstrated, cyclobutenofullerenes were produced as minor products. The results revealed that the class of propargylic phosphate influences its reactivity toward C60. The formation of organophosphate-appended cyclobutanofullerenes is assumed to be mediated by allenol phosphodiester intermediates formed via 6-endo-dig cyclization.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154299