Rhodium-catalyzed synthesis of eight-membered rings.
Experiments to develop a rhodium catalyst for the [4 + 2 + 2] cycloisomerization of dienynes with a second alkyne are described. The generality of the reaction is probed in terms of dienyne structure and alkyne structure. A catalyst system that provides cyclooctatrienes in greater than 70% yield is reported. Several experiments to determine the nature of the catalyst are described.
DeBoef
Brenton
B
Department of Chemistry, Washington University, One Brookings Drive, Saint Louis, Missouri 63130-4899, USA.
Counts
W Richard
WR
Gilbertson
Scott R
SR
D000466:Alkadienes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D034242:Cyclooctanes / Q000138:chemical synthesis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis*; D007536:Isomerism; D008956:Models, Chemical; D012238:Rhodium / Q000737:chemistry*
D000466:Alkadienes; D000480:Alkynes; D034242:Cyclooctanes; D006841:Hydrocarbons, Aromatic; D012238:Rhodium