| Autor: |
Skibiński M; EaStCHEM School of Chemistry and Biomedical Sciences Research Centre, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK. do1@st-andrews.ac.uk snolan@st-andrews.ac.uk., Urbina-Blanco CA, Slawin AM, Nolan SP, O'Hagan D |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2013 Dec 21; Vol. 11 (47), pp. 8209-13. Date of Electronic Publication: 2013 Oct 28. |
| DOI: |
10.1039/c3ob42062k |
| Abstrakt: |
Cyclotetra- and cyclohexa-decane ring systems were prepared with CF2 groups spaced 1,4- and 1,6- for tetradecanes together with 1,5- and 1,6- for hexadecanes. These alicyclic systems were assembled by ring closing metathesis reactions of long terminal diolefins. Ring cyclisation by RCM was promoted by the introduction of the dithiane motif, using a sulfur compatible metathesis catalyst. This gave rise to macrocyclic E-cycloalkanes, which were hydrogenated also using a sulfur compatible catalyst. Finally the dithianes emerged as appropriate precursor motifs for the introduction of difluoromethylene groups. X-Ray structures revealed that the resultant rings have the CF2 groups located only at corner positions and that these groups dictated the overall macrocyclic ring conformations. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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