Tetrahedron p. 2803 - 2816 (1996)
Update date:2022-08-04
Topics:
Araki, Shuki
Hirashita, Tsunehisa
Shimizu, Ken
Ikeda, Takahiro
Butsugan, Yasuo
A variety of α-halo organoindium reagents were prepared in situ from the reaction of gem-dihalo compounds with indium metal, and their reactions with carbonyl compounds and electron-deficient alkenes were examined. The reactions of simple 1,1-diiodoalkanes with indium metal gave no defined products but benzal iodide gave stilbene in a moderate yield. α-Halo organoindium reagents derived from α,α-dibromo carbonyl compounds gave oxiranes and cyclopropanes upon the reactions with aldehydes and alkenes, respectively. 3,3-Dichloropropenes reacted with aldehydes in the presence of indium metal to give the corresponding chlorohydrins and/or homoallylalcohols, depending on the structures of both the dichloropropenes and aldehydes employed.
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