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

Helen M. Sheldrake; Timothy W. Wallace

doi:10.1016/j.tetlet.2007.04.099

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

Helen M. Sheldrake, Timothy W. Wallace

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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. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4407-4411
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.099
Publication status	Published - 18 Jun 2007

Keywords

Allylsulfone
cis-Hydrogenation
Propargylic sulfone
Reduction
Zinc

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10.1016/j.tetlet.2007.04.099

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title = "Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride",

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. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

keywords = "Allylsulfone, cis-Hydrogenation, Propargylic sulfone, Reduction, Zinc",

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AU - Sheldrake, Helen M.

AU - Wallace, Timothy W.

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N2 - 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. © 2007 Elsevier Ltd. All rights reserved.

AB - 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. © 2007 Elsevier Ltd. All rights reserved.

KW - Allylsulfone

KW - cis-Hydrogenation

KW - Propargylic sulfone

KW - Reduction

KW - Zinc

U2 - 10.1016/j.tetlet.2007.04.099

DO - 10.1016/j.tetlet.2007.04.099

M3 - Article

SN - 1873-3581

VL - 48

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EP - 4411

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

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

Abstract

Keywords

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