An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and α-hydroxylmalonate derivatives are obtained selectively using DBU, Na(2)CO(3), and NaOAc as the base, respectively. O(2) was identified to be crucial to the formation of oxetane and α-hydroxylmalonate derivatives.
An efficient protocol for the synthesis of methano[60]fullerene derivatives linked with a single electron‐withdrawing group has been developed through one‐step reaction of [60]fullerene with active halides mediated by CuBr/pentamethyldiethylenetriamine. Many functional groups including esters, ketones, amides, and sulfonyl groups could be easily introduced onto the fullerene skeleton by using this methodology. A plausible reaction mechanism, but not the atom transfer radical process, was proposed for the formation of the methano[60]fullerene derivatives.
Reaction of [60]Fullerene with Epoxides under Photoirradiation: Synthesis of C60-Fused TetrahydrofuranDerivatives. -The cis-isomer (III) is the unexpected major product while in the thermal reaction only the cis-product can be obtained. The substituent Ar 1 has great influence on the reaction rate, whereas the substituent Ar 2 has significant influence on the yield. The two aryl rings and the carbonyl group in the compounds (II) are essential for the photoreaction. No reaction occurs when one of the aryl substituents bears a nitro group. -(MIAO*, C.-B.; TIAN, Z.-Y.; RUAN, X.-J.; SUN, X.-Q.; YANG, H.-T.; Heterocycles 83 (2011) 7, 1615-1620, http://dx.doi.org/10.3987/com-11-12170 ; Sch. Petrochem. Eng., Changzhou Univ.,
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