Masked Alkyne Equivalents for the Synthesis of Mechanically Interlocked Polyynes**
Dr. Przemyslaw Gawel
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Current address: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44/52 Warsaw, Poland
Search for more papers by this authorDr. Steffen L. Woltering
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorDr. Yaoyao Xiong
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorDr. Kirsten E. Christensen
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorCorresponding Author
Prof. Harry L. Anderson
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorDr. Przemyslaw Gawel
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Current address: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44/52 Warsaw, Poland
Search for more papers by this authorDr. Steffen L. Woltering
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorDr. Yaoyao Xiong
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorDr. Kirsten E. Christensen
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorCorresponding Author
Prof. Harry L. Anderson
Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, OX1 3TA UK
Search for more papers by this authorIn memory of François Diederich (1952–2020)
A previous version of this manuscript has been deposited on a preprint server (https://doi.org/10.26434/chemrxiv.13073231.v1).
Abstract
Polyyne polyrotaxanes, encapsulated cyclocarbon catenanes and other fascinating mechanically interlocked carbon-rich architectures should become accessible if masked alkyne equivalents (MAEs) can be developed that are large enough to prevent unthreading of a macrocycle, and that can be cleanly unmasked under mild conditions. Herein, we report the synthesis of a new bulky MAE based on t-butylbicyclo[4.3.1]decatriene. This MAE was used to synthesize a polyyne [2]rotaxane and a masked-polyyne [3]rotaxane by Cadiot–Chodkiewicz coupling. Glaser cyclo-oligomerization of the [2]rotaxane gave masked cyclocarbon catenanes. The unmasking behavior of the catenanes and rotaxanes was tested by photolysis at a range of UV wavelengths. Photochemical unmasking did not proceed cleanly enough to prepare extended encapsulated polyyne polyrotaxanes. We highlight the scope and challenges involved with this approach to interlocked carbon-rich architectures.
Conflict of interest
The authors declare no conflict of interest.
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