Cobalt(I)-catalyzed [6+2] cycloadditions of cyclooctatetra(tri)ene with alkynes.
The cobalt-catalyzed [6+2] cycloaddition of cyclooctatetraene 1 with alkynes 3 affords monosubstituted bicyclo[4.2.2]deca-2,4,7,9-tetraenes 4 in fair to good yields. Due to the valence tautomerism, 1,3,5-cyclooctatriene 2, in equilibrium with bicyclo[4.2.0]octa-2,4-diene A, and alkynes 3 are converted to 10 and 11 according to [6+2] and [4+2] cycloadditions, respectively.
Laboratoire de Synthèse Asymétrique, Université d'Aix-Marseille P. Cézanne, Faculté des Sciences et Techniques de St Jérôme, EGIM, Avenue Escadrille Normandie Niemen, 13397 Marseille Cedex 20, France.
Mathieu
M
Achard
Marc
M
Mosrin
Alphonse
A
Tenaglia
Gérard
G
Buono
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D006572:Heterocyclic Compounds, Bridged-Ring; D009942:Organometallic Compounds; D003035:Cobalt