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 language | English |
|---|---|
| Pages (from-to) | 520-529 |
| Number of pages | 10 |
| Journal | Journal of Organometallic Chemistry |
| Volume | 692 |
| Issue number | 1-3 |
| DOIs | |
| Publication status | Published - Jan 1 2007 |
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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 journal › Article
}
TY - JOUR
T1 - Heterosubstituted cyclopropanation of alkenes with organochromium reagents derived from heterosubstituted dihalomethanes, CrCl2, and tetraalkylethylenediamine
AU - Takai, Kazuhiko
AU - Toshikawa, Shota
AU - Inoue, Atsushi
AU - Kokumai, Ryo
AU - Hirano, Masato
PY - 2007/1/1
Y1 - 2007/1/1
N2 - 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.
AB - 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.
KW - Chromium(II)
KW - Cyclopropane
KW - Cyclopropylsilane
UR - http://www.scopus.com/inward/record.url?scp=33845610175&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33845610175&partnerID=8YFLogxK
U2 - 10.1016/j.jorganchem.2006.06.047
DO - 10.1016/j.jorganchem.2006.06.047
M3 - Article
AN - SCOPUS:33845610175
VL - 692
SP - 520
EP - 529
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
SN - 0022-328X
IS - 1-3
ER -