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Chemistry of acetylenic ethers 69: A new synthesis of di-(alk-1-ynyl) thioethers

✍ Scribed by L. Brandsma


Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
192 KB
Volume
82
Category
Article
ISSN
0165-0513

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✦ Synopsis


Abstract

Di‐(alk‐1‐ynyl) thioethers IV have been prepared from 2,2′‐dichlorodivinyl thioether II by converting this compound into metallated diethynyl thioether by means of four equivalents of sodamide in liquid ammonia, followed by alkylation. The starting material II was obtained in a high yield by partial dehydrochlorination of the adduct I from vinyl chloride and sulphur dichloride. The overall yields are very satisfactory.


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Chemistry of acetylenic ethers LVI Di-(a
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## Abstract A number of di‐(alk‐1‐ynyl) thioethers VIII have been synthesized using reaction scheme 1. Except for diethynyl ether VI the compounds are relatively stable. Reaction scheme 2 has been used to synthesize di‐(prop‐1‐ynyl) ether, a substance exploding at room temperature. An attempt to p

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## Abstract The compounds listed in tables I and II have been prepared by the reaction schemes A, B and C. Acid hydrolysis of vinyloxyethyne produces vinyl acetate. Rearrangement of 3‐hydroxy‐3‐methyl‐1‐vinyloxy‐1‐butyne XIV by acid gives the vinyl ester of 2,2‐dimethylacrylic acid XV.

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## Abstract Di(but‐1‐ynyl)sulphide (IV, R = C~2~H~5~) and di(prop‐1‐ynyl)sulphide (IV, R = CH~3~) have been prepared as outlined in the reaction scheme.