Zur Struktur der Fulvene, II. Darstellung und Eigenschaften von Diarylfulvenen

Abstract

Einige substituierte Diarylfulvene werden hergestellt und aus ihren Eigenschaften Ruckschliisse auf ihre Elektronenstruktur gewonnen.In der I. Mitteilungl) waren physikalische Eigenschaften von p-substituierten 6-Phenyl-fulvenen untersucht worden.

X-ray crystal structures of p-halogenated 6,6-diphenylfulvenes

“…Recrystallisation from ethanol yielded 62% bright red crystals (mp 112°C). Spectroscopic and other analytical data correspond to the specifications from literature [4,19,20] 3 J HH = 10 Hz, 4H, H6); 6.63 (d, 3 J HH = 5 Hz, 2H, H1); 6.26 (d, 3 J HH = 5 Hz, 2H, H2). 13 Crystal structure determination Crystals of the compounds suitable for X-ray analysis were formed by slow evaporation of corresponding solutions of 2-5 in ethanol.…”

Synthesis of fulvenes by reaction of thiobenzophenones with cyclopentadienylmetal carbonyl anions under anhydrous or phase transfer catalyzed conditions

“…Carbon-carbon bond formation and cleavage of the diene-metal bond of 25 would afford the episulfide 26. Desulfurization of the latter by additional anion (7) would give the fulvene. Some evidence against this mechanism comes from the results obtained using the methylcyclopentadienylmetal carbonyl anions (11) where 27, the analogue of M(CO)" 27 24, would be the most stable radical species derived from 11. If 27 was important, the formation of nonmethylated fulvenes or other products was expected.…”

Unexpected Rearrangements of Bicyclic Pyrazolines Derived from 6,6-Diphenylpentafulvene

“…[7] The diarylnitrilimines 2 were prepared in situ by dehydrohalogenation of 1-aryl(chloro)methylene-2-phenylhydrazines. [8,9,10] 6,6-Diphenylpentafulvene (1) was synthesised by condensation of cyclopentadiene with benzophenone in a solution of CH 3 COONa according to G. Kresze et al [11] Cycloadducts 3 and 4. -General Procedure: To a magnetically stirred solution of fulvene 1 (10 mmol) and 1-aryl(chloro)methylene-2-phenylhydrazine 2 (10 mmol) in toluene (60 mL), was added a solution of triethylamine (6 mL) in the same solvent (10 mL) during 5 min.…”