Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl2, and tetraalkylethylenediamine

Kazuhiko Takai, Shota Toshikawa, Atsushi Inoue, Ryo Kokumai, Masato Hirano

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Iodocyclopropanes of trans configuration are produced stereoselectively from terminal alkenes by treatment with a reagent derived from iodoform, chromium(II) chloride, and TEEDA (N,N,N′,N′-tetraethylethylenediamine) in THF. Similarly, cyclopropylsilanes and cyclopropylboronic esters are obtained by using R3SiCHI2, and a combination of Cl2CHB(OR)2 and LiI instead of iodoform, respectively. The heterocyclopropanation occurs selectively at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remain unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions.

Original languageEnglish
Pages (from-to)520-529
Number of pages10
JournalJournal of Organometallic Chemistry
Volume692
Issue number1-3
DOIs
Publication statusPublished - Jan 1 2007

Fingerprint

Alkenes
Ether
alkenes
Olefins
reagents
esters
Ethers
ethers
Esters
Chromium
Amides
Functional groups
amides
Amines
Chlorides
chromium
amines
alcohols
Alcohols
chlorides

Keywords

  • Chromium(II)
  • Cyclopropane
  • Cyclopropylsilane

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl2, and tetraalkylethylenediamine. / Takai, Kazuhiko; Toshikawa, Shota; Inoue, Atsushi; Kokumai, Ryo; Hirano, Masato.

In: Journal of Organometallic Chemistry, Vol. 692, No. 1-3, 01.01.2007, p. 520-529.

Research output: Contribution to journalArticle

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