Photochemical Reduction of F-Adamantyl Halides: A Facile Synthesis of Hydrylfluorocarbons from Chlorofluorocarbons

James L. Adcock, Huimin Luo

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

1-Chloro- and 2-chloro-F-adamantanes, 1,2- and 1,3-dichloro-F-adamantanes, 1,3,5-trichloro-Fadamantane, 1,3,5,7-tetrachloro-F-adamantane, 1-bromo-F-adamantane, and 1-iodo-F-adamantane dissolved in CFCl3 are conveniently dehalogenated in the presence of methanol, hexane, or other hydrogen donor cosolvents by ultraviolet irradiation. The reactions are very clean with isolated yields in the range of 80 %-90 %. Generally, irradiation times increase when large batches of material are photolyzed and when the less reactive secondary F-adamantyl chlorides are reduced. By controlling the irradiation time, polychloro-F-adamantanes can be reduced in a stepwise manner. Only freeradical, not ionic, products are isolated. A possible mechanism for this photochemical reduction is discussed.

Original languageEnglish
Pages (from-to)1115-1118
Number of pages4
JournalJournal of Organic Chemistry
Volume59
Issue number5
DOIs
StatePublished - Mar 1 1994
Externally publishedYes

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