Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

LA Paquette, WE Fristad, DS Dime…

Index: Paquette, Leo A.; Fristad, William E.; Dime, David S.; Bailey, Thomas R. Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 3017 - 3028

Full Text: HTML

Citation Number: 133

Abstract

A general method is described for the formation of vinylsilanes from ketones. Thus, conversion to the benzene-or p-toluenesulfonylhydrazone and sequential treatment with n- butyllithium and chlorotrimethylsilane in anhydrous tetramethylethylenediamine proceeds regiospecifically to afford the less substituted vinylsilane (in unsymmetrical cases). FriedelCrafts acylation with acryloyl chlorides and aluminum chloride and subsequent ...

Related Articles:

Sterically demanding cyclopentadienyl chemistry: synthesis of iron and zirconium complexes of 1-phenyl-3-methyl-4, 5, 6, 7-tetrahydroindenyl

[Batsanov, Andrei S.; Bridgewater, Brian M.; Howard, Judith A.K.; Hughes, Andrew K.; Wilson, Claire Journal of Organometallic Chemistry, 1999 , vol. 590, # 2 p. 169 - 179]

Three-carbon annelations. Regiocontrolled reactivity of trimethylsilyl-and ethoxyethyl-protected cyanohydrins. Versatile homoenolate and acyl anion equivalents

[Jacobson, Richard M.; Lahm, George P.; Clader, John W. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 395 - 405]

Palladium-catalyzed diastereoselective syntheses of (E)-1-trimethylsilyl-2-alkenes,(E)-1-trimethylsilyl-1-alken-3-ynes,(1E, 5E)-1-trimethylsilyl-1, 5-alkadien-3-ynes,(1E, …

[Andreini, Bianca Patrizia; Carpita, Adriano; Rossi, Renzo; Scamuzzi, Barbara Tetrahedron, 1989 , vol. 45, # 17 p. 5621 - 5640]

Organic reactions with polyphosphoric acid—VIII: Intramolecular acylation with lactones (further extension), hydroxy acids and esters

[Kulkarni,S.B.; Dev,S. Tetrahedron, 1968 , vol. 24, p. 553 - 560]

More Articles...