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Unusual pathway of the tantalum-catalyzed carboalumination reaction of alkenes with triethylaluminum.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Nov2013, Vol. 54 Issue 48, p6619-6623. 5p. - Publication Year :
- 2013
-
Abstract
- Abstract: Carboalumination of 1-alkenes (1-hexene, 1-octene, 1-decene) with Et3Al in the presence of catalytic amounts of TaCl5 results in a mixture of 2-(R-substituted)- and 3-(R-substituted)-n-butylaluminums (1:1 ratio) in total yields of 75–85%. The TaCl5-catalyzed reaction of bicyclo[2.2.1]hept-2-ene, endo-tricyclo[5.2.1.02,6]deca-3,8-diene, and (exo/endo)-5-methylbicyclo[2.1.1]hept-2-ene with Et3Al leads to the formation of diethyl[2-exo-(2′-norbornylethyl)]aluminums in high yields. DFT calculations confirm the thermodynamic preference of the final exo product. The multistep reaction mechanisms for the formation of the resultant organoaluminums through tantalacyclopentanes as key intermediates are also discussed. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 54
- Issue :
- 48
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 91600086
- Full Text :
- https://doi.org/10.1016/j.tetlet.2013.09.121