Construction of [4.3.1]propellanes via molybdenum fischer carbene complexes.
Treatment of molybdenum Fischer carbene complexes with 6-methylene-7-octen-1-yne derivatives at 40 degrees C generates substituted tricyclo[4.3.1.0(1,6)]deca-2,4-dienes in good yield. Pentacarbonyl(butylmethoxycarbene)molybdenum(0) afforded the highest cyclization yields (54%), while the analogous chromium carbene complex gave no reaction. The range of dienyne substrates that participate in this reaction is explored and its mechanism is analyzed and discussed.
Bertolini
Thomas M
TM
Department of Chemistry and Biochemistry, 0358, University of California, San Diego, La Jolla, California 92093-0358, USA. tbertoli@uci.edu
Nguyen
Que Huong
QH
Harvey
Daniel F
DF
D002384:Catalysis; D003500:Cyclization; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis*; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D013696:Temperature
D006572:Heterocyclic Compounds, Bridged-Ring; D006838:Hydrocarbons; D011084:Polycyclic Aromatic Hydrocarbons; C030011:carbene; D008982:Molybdenum; D008697:Methane