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Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Nov2014, Vol. 55 Issue 45, p6208-6211. 4p. - Publication Year :
- 2014
-
Abstract
- Mg-promoted reductive silylation of 4-phenyl-3-butyn-2-one in N , N -dimethylformamide (DMF) in the presence of chlorotrimethylsilane brought about double silylation at the β-carbon and oxygen atoms of the carbonyl group to give a multifunctionalized allene with a vinylsilane moiety and a silyl enol ether moiety. A variety of allenes can be synthesized through this simple methodology. Acid-catalyzed hydrolysis of an allene derived from the trimethylsilylation of 4-phenyl-3-butyn-2-one resulted in the formation of the corresponding benzalacetone with a trimethylsilyl group at the β-position of the carbonyl group in high yield. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 55
- Issue :
- 45
- 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 :
- 99060864
- Full Text :
- https://doi.org/10.1016/j.tetlet.2014.09.066