Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions

Marwa M. Aborways; Wesley J. Moran

doi:10.1016/j.tetlet.2014.02.042

Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions

Marwa M. Aborways, Wesley J. Moran

Research output: Contribution to journal › Article › peer-review

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Abstract

The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yields under anhydrous conditions. Conversely, upon addition of water to the reaction mixtures, α,α-dibromoketones and α,α-dichloroketones were formed in good yields, but α,α-diiodoketones were not observed.

Original language	English
Pages (from-to)	2127-2129
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	13
Early online date	24 Feb 2014
DOIs	https://doi.org/10.1016/j.tetlet.2014.02.042
Publication status	Published - 26 Mar 2014

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title = "Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions",

abstract = "The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yields under anhydrous conditions. Conversely, upon addition of water to the reaction mixtures, α,α-dibromoketones and α,α-dichloroketones were formed in good yields, but α,α-diiodoketones were not observed.",

keywords = "Halogenation, Oxidation, Propargyl alcohols, Synthesis",

author = "Aborways, {Marwa M.} and Moran, {Wesley J.}",

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T1 - Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions

AU - Aborways, Marwa M.

AU - Moran, Wesley J.

PY - 2014/3/26

Y1 - 2014/3/26

N2 - The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yields under anhydrous conditions. Conversely, upon addition of water to the reaction mixtures, α,α-dibromoketones and α,α-dichloroketones were formed in good yields, but α,α-diiodoketones were not observed.

AB - The study of the reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions is presented. With sodium iodide, α-iodoenones were formed, however, with sodium bromide or chloride the α-haloenones were only formed in low yields under anhydrous conditions. Conversely, upon addition of water to the reaction mixtures, α,α-dibromoketones and α,α-dichloroketones were formed in good yields, but α,α-diiodoketones were not observed.

KW - Halogenation

KW - Oxidation

KW - Propargyl alcohols

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=84896535005&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.02.042

DO - 10.1016/j.tetlet.2014.02.042

M3 - Article

AN - SCOPUS:84896535005

VL - 55

SP - 2127

EP - 2129

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 13

ER -

Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions

Abstract

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