Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine- mediated active template CuAAC reaction
Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine- mediated active template CuAAC reaction
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
Neal, Edward A.
97630218-70ac-4db3-8cff-c6fbb5195145
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
3 February 2015
Neal, Edward A.
97630218-70ac-4db3-8cff-c6fbb5195145
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Neal, Edward A. and Goldup, Stephen M.
(2015)
Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine- mediated active template CuAAC reaction.
Chemical Science, 6.
(doi:10.1039/c4sc03999h).
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
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Accepted/In Press date: 3 February 2015
Published date: 3 February 2015
Organisations:
Organic Chemistry: SCF
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Local EPrints ID: 376038
URI: http://eprints.soton.ac.uk/id/eprint/376038
ISSN: 1478-6524
PURE UUID: 4332433e-b878-4d71-add4-1dc9fac3469c
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Date deposited: 23 Apr 2015 09:27
Last modified: 14 Mar 2024 19:37
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Author:
Edward A. Neal
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