4.5 Article

Titanium-Catalyzed [6π+2π]-Cycloaddition of Alkynes and Allenes to 7-Substituted 1,3,5-Cycloheptatrienes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 20, Pages 4464-4470

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500442

Keywords

Homogeneous catalysis; Cycloaddition; Fused-ring systems; Allenes; Alkynes

Funding

  1. Russian Foundation for Basic Research [14-03-00167, 15-03-01254]

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The reaction of 7-alkyl(allyl, phenyl)-1,3,5-cycloheptatrienes with alkynes and allenes, catalyzed by the two-component Ti(acac)(2)Cl-2-Et2AlCl system, resulting in the formation of substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]-nona-2,4,7-trienes in up to 90% yield, was accomplished. The structures of the obtained compounds were confirmed by X-ray diffraction and by H-1 and C-13 NMR spectroscopic analysis.

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