Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions

Marwa M. Aborways, Wesley J. Moran

Research output: Contribution to journalArticle

14 Citations (Scopus)

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 languageEnglish
Pages (from-to)2127-2129
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number13
DOIs
Publication statusPublished - 26 Mar 2014

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Sodium Iodide
Sodium Chloride
Sodium
Water
sodium bromide
propargyl alcohol

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Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions. / Aborways, Marwa M.; Moran, Wesley J.

In: Tetrahedron Letters, Vol. 55, No. 13, 26.03.2014, p. 2127-2129.

Research output: Contribution to journalArticle

TY - JOUR

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

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DO - 10.1016/j.tetlet.2014.02.042

M3 - Article

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SP - 2127

EP - 2129

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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