Selective ring opening cross metathesis of cyclooctadiene and trisubstituted cycloolefins

Organic Letters

Volumn 4, Issue 1, 2002, Pages 67-70

  Morgan, John P ^a   Morrill, Christie ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 CYCLOOCTADIENE; 1,5-CYCLOOCTADIENE; ALKADIENE; CYCLOALKANE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKADIENES; CATALYSIS; CYCLOPARAFFINS; MODELS, MOLECULAR; RUTHENIUM;

EID: 0037050473     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016918s     Document Type: Article

References (46)

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33. Alternatively, I may form from the depolymerization of a ROMP oligomer that is rapidly formed during the ROCM of a readily polymerizable monomer.
34. Cyclooctene generally results in lower yields, presumably as a result of its lower ring strain relative to cyclooctadiene. The methyl ketone dimer substrate in Scheme 2 can be produced in low yield from cyclooctene ROCM.
35. If the stoichiometry of the acroyl species is reduced relative to COD, a range of multiple oligomers that contain 4-10 internal alkenes predominates in the product mixtures.
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37. E:Z ratios were determined by comparison of chemical shift data to those of similar compounds reported in Hoye, T. R.; Suhadolnik, J. C. Tetrahedron 1986, 42, 2855-2862.
38. For example, the ring opening metathesis polymerization of 1,5-dimethylcyclooctadiene is considerably slower than that of COD. See ref 3d.
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43. This selectivity model is favored by analogy to similar steric preferences described in Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843-862.
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