83747-02-8Relevant articles and documents
Syntheses with Cyclobutadienes, 19. - Ring Opening of Bi- and Tricyclic Adducts of Carbonyl Compounds onto a Kinetically Stabilized Cyclobutadiene
Fink, Juergen,Guembel, Helmut,Eisenbarth, Philipp,Regitz, Manfred
, p. 1027 - 1038 (2007/10/02)
Benzophenone (6) adds photochemically onto the cyclobutadiene 5b to give the oxabicyclohexene 7 which is in equilibrium with the oxatricyclohexane 8 in acidic medium.The reaction of fluorenone (11) with 5b is comparable (formation of 12 and 13) but the bicyclic compound undergoes spontaneous ring opening reaction to the 1,3-diene 14.The latter one isomerizes photochemically by electrocyclic ring closure to the cyclobutene 15; this process is reversible thermally.The cyclopropenone 16 only reacts slowly at room temperature with 5b; instead of the primary adduct 17 the isomeric trifulvene 18 is isolated.Under the influence of trifluoroacetic acid the oxabicyclohexenes (7->19,21a,c,d->22a,c,d) as well as the oxatricyclohexanes (8->19, 13->14) undergoing ring opening reactions to the corresponding 1,3-dienes.Crystal structure analyses have been performed for 18 and 22a.