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A Solid-State Intramolecular Wittig Reaction Enables Efficient Synthesis of Endofullerenes Including Ne@C60 , 3 He@C60 , and HD@C60.

ABSTRACT: An open-cage fullerene incorporating phosphorous ylid and carbonyl group moieties on the rim of the orifice can be filled with gases (H2 , He, Ne) in the solid state, and the cage opening then contracted in situ by raising the temperature to complete an intramolecular Wittig reaction, trapping the atom or molecule inside. Known transformations complete conversion of the product fullerene to C60 containing the endohedral species. As well as providing an improved synthesis of large quantities of 4 He@C60 , H2 @C60 , and D2 @C60 , the method allows the efficient incorporation of expensive gases such as HD and 3 He, to prepare HD@C60 and 3 He@C60 . The method also enables the first synthesis of Ne@C60 by molecular surgery, and its characterization by crystallography and 13 C NMR spectroscopy.

SUBMITTER: Hoffman G 

PROVIDER: S-EPMC8048630 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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A Solid-State Intramolecular Wittig Reaction Enables Efficient Synthesis of Endofullerenes Including Ne@C<sub>60</sub> , <sup>3</sup> He@C<sub>60</sub> , and HD@C<sub>60</sub>.

Hoffman Gabriela G   Walkey Mark C MC   Gräsvik John J   Bacanu George R GR   Alom Shamim S   Bloodworth Sally S   Light Mark E ME   Levitt Malcolm H MH   Whitby Richard J RJ  

Angewandte Chemie (International ed. in English) 20210304 16

An open-cage fullerene incorporating phosphorous ylid and carbonyl group moieties on the rim of the orifice can be filled with gases (H<sub>2</sub> , He, Ne) in the solid state, and the cage opening then contracted in situ by raising the temperature to complete an intramolecular Wittig reaction, trapping the atom or molecule inside. Known transformations complete conversion of the product fullerene to C<sub>60</sub> containing the endohedral species. As well as providing an improved synthesis of  ...[more]

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