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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 15, Number 10
BKCSDE 15(10)
October 20, 1994 

Mono-dehalogenation of gem-Dihalocyclopropanes Using Tetracarbonylhydridoferrate
Sang Chul Shim*, Seung Yub Lee, Dong Yub Lee, Heung-Jin Choi
Tetracarbonylhydridoferrate, HFe(CO)4-, generated by the reaction of Fe(CO)5 with alkaline solution, is a good reducing agent for mono-dehalogenation of gem-dihalocyclopropanes. It also acts as a good reducing catalyst under phase transfer reaction conditions. 1,1-Dibromo-2-phenylcyclopropane and 1,1-dichloro-2-phenylcyclopropane were reduced to the corresponding mono-dehalogenated products in excellent yields. Thermodynamically stable trans-l-bromo-2-phenyl cyclopropane was formed as the major product over the cis-isomer, trans/cis=3/2. The 1-bromo-2-phenyl cyclopropane radical intermediate was formed by single electron transfer from HFe(CO)4-. Dissociation of bromide anion, followed abstraction of hydrogen radical from alcoholic solvent would lead to the formation of the stable trans-isomer. The further mechanistic aspects were discussed.
845 - 849
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