TY - JOUR
T1 - Photochemical Reduction of F-Adamantyl Halides
T2 - A Facile Synthesis of Hydrylfluorocarbons from Chlorofluorocarbons
AU - Adcock, James L.
AU - Luo, Huimin
PY - 1994/3/1
Y1 - 1994/3/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0000718427&partnerID=8YFLogxK
U2 - 10.1021/jo00084a032
DO - 10.1021/jo00084a032
M3 - Article
AN - SCOPUS:0000718427
SN - 0022-3263
VL - 59
SP - 1115
EP - 1118
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -