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Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM)

(2013) ORGANIC & BIOMOLECULAR CHEMISTRY. 11(47). p.8209-8213
Author
Organization
Abstract
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.
Keywords
OLEFIN METATHESIS, RUTHENIUM-INDENYLIDENE COMPLEXES, BEARING, LIGANDS, KETONES

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Chicago
Skibinski, Maciej, César Alejandro Urbina Blanco, Alexandra MZ Slawin, Steven Nolan, and David. O’Hagan. 2013. “Synthesis and Structure of Large Difluoromethylene Containing Alicycles by Ring Closing Metathesis (RCM).” Organic & Biomolecular Chemistry 11 (47): 8209–8213.
APA
Skibinski, M., Urbina Blanco, C. A., Slawin, A. M., Nolan, S., & O’Hagan, D. (2013). Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM). ORGANIC & BIOMOLECULAR CHEMISTRY, 11(47), 8209–8213.
Vancouver
1.
Skibinski M, Urbina Blanco CA, Slawin AM, Nolan S, O’Hagan D. Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM). ORGANIC & BIOMOLECULAR CHEMISTRY. 2013;11(47):8209–13.
MLA
Skibinski, Maciej, César Alejandro Urbina Blanco, Alexandra MZ Slawin, et al. “Synthesis and Structure of Large Difluoromethylene Containing Alicycles by Ring Closing Metathesis (RCM).” ORGANIC & BIOMOLECULAR CHEMISTRY 11.47 (2013): 8209–8213. Print.
@article{8166430,
  abstract     = {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.},
  author       = {Skibinski, Maciej and Urbina Blanco, C{\'e}sar Alejandro and Slawin, Alexandra MZ and Nolan, Steven and O'Hagan, David.},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {OLEFIN METATHESIS,RUTHENIUM-INDENYLIDENE COMPLEXES,BEARING,LIGANDS,KETONES},
  language     = {eng},
  number       = {47},
  pages        = {8209--8213},
  title        = {Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM)},
  url          = {http://dx.doi.org/10.1039/c3ob42062k},
  volume       = {11},
  year         = {2013},
}

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