77884-49-2

Upstream product

• 26307-17-5 2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dienone 
• 70216-50-1 1,6,7,8,9,9-hexachloro-endo-tricyclo<4.2.1.0^2.5>nona-3,7-diene 

Downstream Products

• 77884-51-6 (5Z,7Z,9Z)-(1S,4R,4aR,10aS)-1,2,3,4,11,11-Hexachloro-6,9-dimethyl-7,8-diphenyl-1,4,4a,10a-tetrahydro-1,4-methano-benzocyclooctene 
• 77884-50-5 endo-anti-1,10,11,12,13,13-hexachloro-4,7-dimethyl-5,6-diphenyl-tetracyclo<8,2,1,0^2,90^3,8>triadeca-4,6,11-triene 
• 77300-35-7 C₂₇H₂₀Cl₆ 
• 108312-57-8 C₂₇H₂₀Cl₆O₂ 

Relevant academic research and scientific papers

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

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. bicyclooctadienes.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.

PERICYCLIC TRANSFORMATIONS OF TETRACYCLO2,903,8>TRIDECA-4,6,11-TRIENES, AND FORMATION OF DIHYDROSEMIBULLVALENES BY THERMAL INTRAMOLECULAR?4a+?2a>CYCLOADDITION IN SUBSTITUTED CYCLOOCTATRIENES

Cyclopentadienones react with certain cyclobutene dienophiles to give the anticipated carbonyl bridge adducts; these, on relatively mild thermolysis, yield dihydrosemibullvalene derivatives by a novel sequence including cheletropic loss of carbon monoxide, electrocyclic ring opening of immediate substituted bicyclooctadienes, and intramolecular ?4a + ?2a>cycloaddition of the derived cyclooctatrienes.Other pericyclic reactions of compounds related to those of the title compounds are also discussed.