35377-95-8

Upstream product

• 25603-67-2 9-phenyl-fluoren-9-ol 
• 101937-03-5 9-phenyl-fluoren-9-yl hydroperoxide 
• 76-84-6 triphenylmethyl alcohol 
• 56-23-5 tetrachloromethane 
• 55135-66-5 9-bromo-9-phenyl-9H-fluorene 
• 7803-57-8 hydrazine hydrate 
• 59110-36-0 9,9'-diphenyl-9,9'-bifluorene 
• 71-43-2 benzene 
• 25022-99-5 9-chloro-9-phenyl-9H-fluorene 
• 60-29-7 diethyl ether 

Relevant academic research and scientific papers

Self-Initiated Autoxidation of a Sterically Crowded Cycloheptatriene Derivative via Norcaradienyloxyl Radicals

An extremely crowded cycloheptatriene derivative, 1,3,5-tri-tert-butyl-7-(9-phenyl-9-fluorenyl)-l,3,5-cycloheptatriene (1), underwent autoxidation at 25 °C in cyclohexane to give 4-tert-butyl-2-pivaloylphenol (3) (33%), 5-tert-butyl-2-pivaloylphenol (4) (11%), 1,3,5-tri-tert-butylbenzene (5) (5%), tert-butyl 9-phenyl-9-fluorenyl peroxide (6) (44%), bis(9-phenyl-9-fluorenyl) peroxide (7) (7%), 1,1′,3,3′,5,5′-hexa-tert-butyl-7,′-bicycloheptatriene (8) (2%), and carbon monoxide (4%). ESR studies showed that 1 dissociates into l,3,5-tri-tert-butyltropyl radical (11) and 9-phenylfluorenyl radical (12) at 25-85 °C. The enthalpy and entropy of dissociation were determined to be 23.3 kcal/mol and 22.0 cal/mol·K, respectively. The formation of 3-5 can be explained by a mechanism involving attack of molecular oxygen to 11 and subsequent valence tautomerism of cycloheptatrienyloxyl radicals to norcaradienyloxyl radicals.

Synthesis of o-Substituted Phenols by Criegee Rearrangement of Benzylic Hydroperoxides

9-Phenylthioxanthen-9-ol, 10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol, and 9-arylfluoren-9-ols undergo Criegee-type rearrangements when treated with hydrogen peroxide and acid to generate substituted benzophenones from the first two substrates, and monoesters of biphenyl-2,2'-diol from the fluorenes via subsequent Bayer-Villiger oxidation of the intermediate 2'-aroylbiphenyl-2-ol. 5-Phenyl-10,11-dihydrodibenzocyclohepten-5-ol and its dehydroderivative gave the corresponding heptanone and heptenone on treatment with acid and hydrogen peroxide.Prolonged reaction of the 5-phenyldibenzohepten-5-ol afforded products arising from oxidation of the double bond.