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Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction.

ABSTRACT: We recently identified competitive formation of doubly interlocked [3]rotaxanes as the origin of the non-linear variation in yield of [2]rotaxane with macrocycle size in the bipyridine-mediated AT-CuAAC reaction. Selection of reaction conditions gave [2]rotaxanes in essentially quantitative yield in all cases and hard to access doubly threaded [3]rotaxanes in up to 50% yield in a single, four component coupling. Based on the effect of macrocycle structure on the reaction outcome we propose a detailed mechanism of [3]rotaxane formation.

SUBMITTER: Neal EA

PROVIDER: S-EPMC5645920 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction.

Neal Edward A EA Goldup Stephen M SM

Chemical science 20150203 4

We recently identified competitive formation of doubly interlocked [3]rotaxanes as the origin of the non-linear variation in yield of [2]rotaxane with macrocycle size in the bipyridine-mediated AT-CuAAC reaction. Selection of reaction conditions gave [2]rotaxanes in essentially quantitative yield in all cases and hard to access doubly threaded [3]rotaxanes in up to 50% yield in a single, four component coupling. Based on the effect of macrocycle structure on the reaction outcome we propose a det ...[more]

PMID: 29308153

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