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Stereoselective Iodocyclopropanation of Terminal Alkenes With Iodoform, chromium(II) Chloride, and N,N,N',N'-tetraethylethylenediamine

Stereoselective Iodocyclopropanation of Terminal Alkenes With Iodoform, chromium(II) Chloride, and N,N,N',N'-tetraethylethylenediamine

Kazuhiko Takai, Shota Toshikawa, Atsushi Inoue, Ryo Kokumai

J Am Chem Soc. 2003 Oct 29;125(43):12990-1.

PMID: 14570448

Abstract:

Chemoselectivity of a reagent for (E)-olefination of aldehydes derived by reduction of iodoform with chromium(II) chloride in THF changes markedly by addition of TEEDA (N,N,N',N'-tetraethylethylenediamine), and trans-iodocyclopropanes are produced stereoselectively from terminal alkenes by treatment with the base-added reagent system. The iodocyclopropanation occurs only at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remained unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10049055	Chromium(II) chloride		10049-05-5	Price

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