Tetrahedron letters

Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride

HM Sheldrake, TW Wallace

Index: Sheldrake, Helen M.; Wallace, Timothy W. Tetrahedron Letters, 2007 , vol. 48, # 25 p. 4407 - 4411

Full Text: HTML

Citation Number: 19

Abstract

Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF–water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways.

Related Articles:

Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides

[Bahrami, Kiumars; Khodaei, Mohammad M.; Sohrabnezhad, Samira Tetrahedron Letters, 2011 , vol. 52, # 48 p. 6420 - 6423]

Alkynes as masked ylides: gold-catalysed intermolecular reactions of propargylic carboxylates with sulfides

[Davies, Paul W.; Albrecht, Sebastien J.-C. Chemical Communications, 2008 , # 2 p. 238 - 240]

Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno-and thioesters

[Gul, Kashif; Narayanaperumal, Senthil; Dornelles, Luciano; Rodrigues, Oscar E.D.; Braga, Antonio Luiz Tetrahedron Letters, 2011 , vol. 52, # 28 p. 3592 - 3596]

Zn in ionic liquid: an efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters

[Narayanaperumal, Senthil; Alberto, Eduardo E.; Gul, Kashif; Kawasoko, Cristiane Yuriko; Dornelles, Luciano; Rodrigues, Oscar E.D.; Braga, Antonio Luiz Tetrahedron, 2011 , vol. 67, # 25 p. 4723 - 4730]

A “tag-and-modify” approach to site-selective protein modification

[Lin, Yuya A.; Chalker, Justin M.; Floyd, Nicola; Bernardes, Goncalo J. L.; Davis, Benjamin G. Journal of the American Chemical Society, 2008 , vol. 130, # 30 p. 9642 - 9643]

More Articles...