2,6- Dimethoxyanthracene - A Directing Group for Regioselective Bisaddition to C60

Wilson, Stelios

doi:10.1016/00404-0399(50)1111t-

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2017

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“…In this way an increased contribution of cis-isomers was achieved, but without significant selectivity. 5 The first double cycloaddition to C 60 directed by the substrate was carried out by combining two cycloadditions, Bingel and Diels-Alder, with regioselective production of the equatorial isomer with an excellent yield of 50%. 6 Most of the regioselective syntheses of fullerene bisadducts are now based on tethers with two reactive moieties directing to the desired positions using Bingel, 1c,7 Diels-Alder 1d,4b and Prato 4a,8,9 cycloaddition reactions.…”

Section: Controlledmentioning

confidence: 99%

Fullerene bisadduct regioisomers containing an asymmetric diamide tether

et al. 2017

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Four macrocyclic bis(pyrrolidino)fullerene regioisomers with e-edge, e-face, trans-4 and cis-2 addition patterns were synthesized from the corresponding monoadduct by Prato's cycloaddition in a yield of 50%, and fully characterized by spectroscopic techniques. Bisadduct regioisomers were isolated easily in a pure form using dry-flash column chromatography. The relative ratio of the isolated regioisomers e-edge/e-face/trans-4/cis-2 was 1.0:1.9:1.5:4.9. Morphology of selfassembled structures of the four bisadduct regioisomers in solution was characterized using scanning electron microscopy.

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Section: Controlledmentioning

confidence: 99%