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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Thermal [2+2] cycloaddition of morpholinoenamines with C60 via a single electron transfer
Tsubasa Mikie1, Haruyasu Asahara, Kazuaki Nagao
1Division of Applied Chemistry, Graduate School of Engineering, Osaka University 2-1, Yamadaoka, Suita, Osaka 565-0871, Japan.
Abstract:
The thermal reaction of C(60) with five- and six-membered morpholinocycloalkenes in refluxing toluene exclusively gave the [2+2] cycloadducts in high yields. However, a seven-membered homologue sluggishly reacted with C(60) because of the increasing steric hindrance. This cycloaddition reaction is likely to proceed via a single electron transfer (SET), a radical-coupling, and subsequent ion cyclization rather than the prior proton transfer between the radical ions.
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