Synthesis of fluorinated derivatives of benzo[k]fluoranthene and indeno[1,2,3-cd]pyrene and 8,9-dihydro-8,9-epoxybenzo[k]fluoranthene

Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation

“…In contrast with the successful cyclizations of the above substrates, acenaphthene derivative 28 , prepared by Wittig olefination of acenaphthenequinone followed by catalytic hydrogenation, led only to traces of cyclized product 30 (Scheme ). The crude reaction mixtures showed that 28 suffered dehydrogenation and reductive elimination of the bromide as the major decomposition pathways.…”

Synthesis and Reactions of Acenaphthenequinones-Part-2. The Reactions of Acenaphthenequinones

“…Wittig reaction of bis(triphenylphosphonium) dibromides with 1 under phase-transfer conditions gave 112 ( Scheme 29 ) [ 92 ].…”

Synthesis and Reactions of Acenaphthenequinones. Part 2. The Reactions of Acenaphthenequinones

“…Compound 111 was isolated in only one configuration and its formation may arise either via the o-quinomethaneylide intermediate 109 or the monoylide 108. Intramolecular Witting reaction of 109 gave 110.Scheme 28Wittig reaction of bis(triphenylphosphonium) dibromides with 1 under phase-transfer conditions gave 112 (Scheme 29)[92].Scheme 29Reaction of 113 with hydroxylamine gave the oxime 114 and the pyrrole derivative 115, whereas its reaction with hydrazines afforded the pyridazinones 116 (Scheme 30)[93]. Reaction of the monoxime of 1 with Ph 3 P=CHCO 2 Me afforded stereoisomeric products of 114, whereas the reaction with ylide Ph 3 P=CHCOMe gave the pyridine derivatives 118.…”