Elimination to alkynes
11 real reactions from the literature, on vicinal dihalides, vinyl bromides and vinyl chlorides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Elimination to alkyne: 2,3-dibromopropionaldehyde diethyl acetal (a vicinal dihalide) with KOH; H2O, pentane gives 3,3-diethoxypropyne (the terminal alkyne).
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Elimination to alkyne: 10,11-dibromoundecanoic acid (a vicinal dihalide) with 1) NaNH2 (3 equiv), Δ; 2) H3O+ (HCl, H2O) gives 10-undecynoic acid (the terminal alkyne).
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Elimination to alkyne: (1,2-dibromo-2-phenylethyl)benzene (a vicinal dihalide) with KOH, CH3CH2OH; Δ gives diphenylacetylene (the internal alkyne).
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Elimination to alkyne: a vicinal dihalide with Chin. J. Chem. 2011, 29, 2350; K2CO3; DMSO; 12 hr 115 ºC gives phenylacetylene (the terminal alkyne).
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Elimination to alkyne: ethyl 2,3-dibromo-3-phenylpropanoate (a vicinal dihalide) with KOH; CH3CH2OH, Δ gives potassium 3-phenylpropiolate (the internal alkyne).
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Elimination to alkyne: 9,10-dibromo-stearic acid (a vicinal dihalide) with Na (3 equiv.); NH3 gives sodium stearolate (the internal alkyne).
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Elimination to alkyne: 2,3-dibromosuccinic acid (a vicinal dihalide) with 1) KOH; 2) H2SO4 (excess) gives 2-butynedioic acid (the internal alkyne).
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Elimination to alkyne: (1,2-dibromoethyl)benzene (a vicinal dihalide) with Na, NH3 gives phenylacetylene (the terminal alkyne).
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Elimination to alkyne: (2Z)-1,3-dichloro-2-butene (a vinyl chloride) with KOH, 170 °C; ethylene glycol, n-butyl Cellosolve gives vinyl acetylene (the terminal alkyne).
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Elimination to alkyne: trans-beta-bromostyrene (a vinyl bromide) with KOH; 200 °C gives phenylacetylene (the terminal alkyne).
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Elimination to alkyne: 3-cyclohexyl-2-bromopropene (a vinyl bromide) with NaNH2, Δ; mineral oil gives (prop-2-yn-1-yl)cyclohexane (the terminal alkyne).