The Nuclear Halogenation of Fluorene, Fluorenone, Acenaphthene, and Acenaphthenequinone by N-Bromosuccinimide and N-Chlorosuccinimide

Inclusion Compounds of Diol Hosts Featuring Two 9-Hydroxy-9-fluorenyl or Analogous Groups Attached to Linear Spacer Units

“…Starting compounds fluorenone (16a), xanthone (18a) thioxanthone (18b), dibenzosuberone (18c), dibenzosuberenone (18d), p-dibromobenzene, and 4,4Ј-dibromobiphenyl were purchased from Janssen. 2,7-Di-tert-butylfluorenone (16b), [36,63] 2,7-dichlorofluorenone (16c), [46] 2,7-dibromo-fluorenone (16d), [36,64] and 4,4ЈЈ-dibromo-1,1Ј:4Ј,1ЈЈ-terphenyl [65] were prepared according to literature procedures.…”

“…The starting ketones 16b and 16d (Scheme 4) were obtained by oxidation of the corresponding fluorenones with O 2 , [36,45] and 16c by chlorination of fluorenone with NCS. [46] The ethynyl-substituted fluorenols 17a and 17b were prepared from fluorenones 16a and 16b, with ethylmagnesium bromide and ethyne in dry THF [47,48] to yield compound 2 as a by-product of 17a.…”

Electro-organic reactions. Part 20. Electrogenerated bases, ylide formation, and Wittig alkene synthesis

“…Preparation of the Probases (l).-The dicyano-substituted probases (la) and (lb) were prepared from the appropriate fluorenone and malononitrile by standard literature methods.2' The 2,7-dibromofluorenone required for the preparation of (lb) was prepared by bromination of fluorenone using Nbromosuccinimide. 22 The probase (1 c) was obtained from the reaction between ethylcyanoacetate and fluorenone using the procedure of Cragoe et Preparative EZectro2yses.-The procedure used for the preparation of stilbene and 1,6diphenylbutadiene via ylide formation by electrogenerated base has been de~cribed.~ G.1.c. analysis (Hewlett-Packard 5830A, column 5% OV-17) was carried out on the crude product mixtures to which a known weight of biphenyl had been added as an internal standard; the detector response factor for each of the products was determined with respect to biphenyl.…”

Inclusion Compounds of Bulky Binaphthyl-type Bis-fluorenol Hosts

“…Starting compounds 3,3 0 -dibromo-2,2 0 -binaphthyl [15], 2,7-dichloro-9-fluorenone [33], 2,7-dibromo-9-fluorenone [34] and 2,7-di-t-butyl-9-fluorenone [35] were prepared following the literature descriptions. 9-Fluorenone was purchased from Acros.…”