ChemInform Abstract: FLUORIERUNG VON ADAMANTAN MIT XENONDIFLUORID

Functionalization of Organic Molecules by Xenon Fluorides

“…Fluorination of adamantane results in the formation of four products, from whose distribution it is evident that the difference in the reactivity between the secondary and the tertiary carbon atom is much larger than the difference between the reactivities of the primary and secondary carbon atoms of hexane. Liquid-phase functionalization of a tertiary carbon atom is observed in reactions in carbon disulfide, where 1-fluoroadamantane is formed 17 .…”

Reactions of adamantanes in electrophilic media

“…The complex 32 with the five-coordinate carbon is assumed to be formed in the attack of the nitronium cation on adamantane, which then decomposes to give 1-fluoroadamantane (33). can also be prepared by the reaction of adamantane (1) with xenon fluoride 40 or with ClF 3 . 41 In the latter case, 1,3-difluoro-and 1,3,5-trifluoro-adamantanes were formed together with the 1-fluoroadamantane (33).…”

“…1,3,5,7-Tetrachloroadamantane (40) has been obtained by heating 1,3,5-trichloroadamantane (37) with chlorosulfonic acid for 150 h at 70 8C. 54 Chlorination of adamantane (1) and its homologues can be accomplished with alkyl halides in the presence of Lewis acids.…”

“…56 A mixture of 1-chloro-( 35) and 1,3-dichloro-adamantanes (36) was formed in the reaction of adamantane (1) with CCl 4 in the presence of AlCl 3 at 20 8C. 57 1,3,5,7-Tetrachloroadamantane (40) was prepared in 55% yield by refluxing adamantane (1) with AlCl 3 in CCl 4 . 58 The reaction of adamantane (1) with AlCl 3 in CCl 4 for 4 h at 20 8C affords 1,3-dichloroadamantane (41) in 49% yield.…”