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Studies on sulfinatodehalogenation: XVI. Sodium dithionite‐initiated addition of perfluoroalkyl iodides to terminal alkynes
Author(s) -
WeiYuan Huang,
Long LÜ,
YuanFa Zhang
Publication year - 1990
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19900080411
Subject(s) - chemistry , sodium dithionite , adduct , yield (engineering) , bromide , medicinal chemistry , organic chemistry , metallurgy , materials science
Reaction of perfluoroalkyl iodides with a series of alkynes under sulfinatodehalogenation condition gave a mixture of E / Z adducts very readily in high yield, thus constituted a mild, convenient and effective new method for the addition of perfluoroalkyl iodides to alkynes. Under the same condition, in the presence of 1‐hexyne perfluoroalkyl bromide and 1,1,1‐trichlorotrifluoroethane reacted only to give sulfinates as the major products. A radical mechanism was proposed for the addition reaction.