New Aryl-substituted 1,4-Dioxanes Prepared from Propargyl Ethers of (Bromomethyl)(phenylalkyl)methanols.

The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity. 6 Reactions Related to Catalytic Alkyne Hydration 7 Conclusions and Outlook

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“…Other alkyl halogenides give regular results. 233 1-Bromo-and 1-iodoalkynes are hydrated to ahaloketones. 234…”

Section: Terminal Alkynes Bearing Halogen and Other Functionalitymentioning

confidence: 99%

Catalytic Hydration of Alkynes and Its Application in Synthesis

Hintermann¹,

Labonne²

2007

Synthesis

398

261

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“…Alkoxyhalogenation of alkenes [1,2] w i t h C 3 -unsaturated alcohols is a common method for the synthesis of unsaturated β-halogenethers which are used in the synthesis of heterocyclic compounds [4][5][6] and biologically active preparations [3][4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Haloalkoxylation of 3-Organyloxy-1-Propenes in Dimethylacetylenecarbinol Medium

Ezizbeyli¹,

Talybov²,

Mammadbayli³

2020

Chemical Problems

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Reaction of alkoxyhalogenation 3-organyloxy-1-propenes with N-bromosuccinimide (or iodine) in dimethylacetylenecarbinol medium proceeds regioselectively according to NMR spectra. It proceeds at a low temperatureç cooling the reaction mixture with ordinary ice. The main reaction products, diethers -3-bromo (iodine) -1,2-propanediol, are formed in high yields. İt founded that the alkoxyhalogenation of allyl ethers with propinol proceeds regioselectively with fixation of the halogen atom to the peripheral carbon atom of C=C bond. The yields of bromine-containing products are higher than those for iodine analogues. Iodine-containing products boil at a higher temperature than bromine analogues. In the reaction products, substances with the replacement of the halogen atom with unsaturated alcohol are not observed. The reaction was monitored by means of thin layer chromatography. Similar synthesized compounds are used as biologically active compounds.

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