AI Article Synopsis
- A new two-step method has been developed to convert norbornadiene (NBD) into its most stable dimer, heptacyclo[6.6.0.0.0.0.0.0] tetradecane (HCTD).
- The process begins with a Rh-catalyzed Diels-Alder reaction that forms an exo-cis-endo dimer, which then transforms into HCTD through acid treatment.
- The study also explores creating 7,12-disubstituted cages from 7-(alkyl/aryl) NBDs and the selective post-synthetic modification of HCTD at specific carbon positions.
Article Abstract
A selective and scalable two-step approach to the dimerization of norbornadiene (NBD) into its thermodynamically most stable dimer, heptacyclo[6.6.0.0 .0 .0 .0 .0 ] tetradecane, (HCTD) is reported. Calculations indicate that the reaction starts with the Rh-catalyzed stepwise homo Diels-Alder cyclisation of NBD into its exo-cis-endo dimer. Treatment of this compound with acid promotes its evolution to HCTD via a [1,2]-sigmatropic rearrangement. The assemblies of 7,12-disubstituted cages from 7-(alkyl/aryl) NBDs, as well as the selective post-synthetic C-H functionalization of the core HCTD scaffold at position C1, or positions C1 and C4 are described.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756769 | PMC |
| http://dx.doi.org/10.1002/anie.202010766 | DOI Listing |
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Article Synopsis
- A new two-step method has been developed to convert norbornadiene (NBD) into its most stable dimer, heptacyclo[6.6.0.0.0.0.0.0] tetradecane (HCTD).
- The process begins with a Rh-catalyzed Diels-Alder reaction that forms an exo-cis-endo dimer, which then transforms into HCTD through acid treatment.
- The study also explores creating 7,12-disubstituted cages from 7-(alkyl/aryl) NBDs and the selective post-synthetic modification of HCTD at specific carbon positions.
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