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Synthesis and Rearrangement of Alkylaryl- and Aryl-substituted Dihydrosemibullvalenes by Thermolysis of 7,8-Fused Cyclo-octa-1,3,5-triene Derivatives

DOI: 10.1039/P29860001651

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1651 - 1666 (1986)

Update date:2022-08-05

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Authors:

Greenfield, SimonGreenfield, Simon

Mackenzie, KennethMackenzie, Kenneth

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Article abstract of DOI:10.1039/P29860001651

The thermal cycloaddition of a cyclobuteno-dienophile (1) with cyclopentadienones has been systematically investigated; the stereoisomeric adducts give convenient access by decarbonylation to a variety of tetra-aryl, methyltriphenyl-, triphenyl-, tri-t-butyl-, and dimethyldiphenyl-cyclo-octa-1,3,5-triene derivatives as the products of electrocyclic ring-opening of the valence-tautomeric primary products of cheletropic bridge-extrusion, viz. bicyclo<4.2.0>octadienes.These compounds provide useful models for investigation of equilibria between the electrocyclic valence tautomers, the scope and mechanism for thermal cross-cyclisations in, for example, unsymmetrically substituted cyclooctatrienes, and the thermal vinyl-cyclopropane (1,3-allylic shift) isomerisation and/or H-atom transfer disproportionation of the resulting arylated and alkylaryldihydrosemibullvalenes.The results best accord with diradical pathways for cyclo-octatriene-dihydrosemibullvalene conversions and subsequent rearrangements.Usefull 13C and 1H n.m.r. structure correlations and new examples of cyclopentadienones are also reported.

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Product name:2,4-bis-(p-methoxyphenyl)-3,5-diphenylcyclopenta-2,4-dienone

Cas No:92085-48-8

92085-48-8

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