Details
| Original language | English |
|---|---|
| Pages (from-to) | 3799-3806 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 22 |
| Publication status | Published - 2000 |
Abstract
A mixture of samarium(II) iodide and samarium can induce a coupling reaction of three molecules of alkanoyl halide to give trialkylcarbinols of 2-hydroxy-1,3-diones. When aliphatic, unbranched alkanoyl chlorides are used, this new coupling reaction provides trimeric products as the main reaction products. Tetrahydropyran (THP) proved superior as the solvent because no ring-opening and subsequent reaction with the alkanoyl halides was observed under the reaction conditions, unlike when THF was used.
Keywords
- Alkanoyl halide, Coupling, Samarium, Samarium(II) iodide, Trimerization
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 22, 2000, p. 3799-3806.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - New coupling reactions of some acyl chlorides with samarium diiodide in the presence of samarium
T2 - Carbinols from three acyl units
AU - Clausen, Christian
AU - Weidner, Ingo
AU - Butenschön, Holger
PY - 2000
Y1 - 2000
N2 - A mixture of samarium(II) iodide and samarium can induce a coupling reaction of three molecules of alkanoyl halide to give trialkylcarbinols of 2-hydroxy-1,3-diones. When aliphatic, unbranched alkanoyl chlorides are used, this new coupling reaction provides trimeric products as the main reaction products. Tetrahydropyran (THP) proved superior as the solvent because no ring-opening and subsequent reaction with the alkanoyl halides was observed under the reaction conditions, unlike when THF was used.
AB - A mixture of samarium(II) iodide and samarium can induce a coupling reaction of three molecules of alkanoyl halide to give trialkylcarbinols of 2-hydroxy-1,3-diones. When aliphatic, unbranched alkanoyl chlorides are used, this new coupling reaction provides trimeric products as the main reaction products. Tetrahydropyran (THP) proved superior as the solvent because no ring-opening and subsequent reaction with the alkanoyl halides was observed under the reaction conditions, unlike when THF was used.
KW - Alkanoyl halide
KW - Coupling
KW - Samarium
KW - Samarium(II) iodide
KW - Trimerization
UR - http://www.scopus.com/inward/record.url?scp=0141964984&partnerID=8YFLogxK
U2 - 10.1002/1099-0690(200011)2000:22<3799::AID-EJOC3799>3.0.CO;2-N
DO - 10.1002/1099-0690(200011)2000:22<3799::AID-EJOC3799>3.0.CO;2-N
M3 - Article
AN - SCOPUS:0141964984
SP - 3799
EP - 3806
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 22
ER -