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Orientation in the nucleophilic addition of mercaptans to 2-methyl-1-butene-3-yne

✍ Scribed by Thomas L. Jacobs; Alexander Mihailovski

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
253 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the course of studying the chemical properties of 1-thioethoxy-3-methyl-l,L-butadiene (I) we observed the rearrangement of this compound on gas liquid chromatography columns to a 1,3-diene (reaction 1) whose properties were identical to those of the addition product from 2-methyl-l-buten-3-yne and ethyl mercaptide ion. This adduct was reported(l) to be 3-methyl-2-thioethoxy-1,3-butadiene (II). The reaction of mercaptide ions with acetylenes has been reported to give trans addition. With terminal acetylenes the alkylthio group is sometimes found on the terminal carbon, sometimes on the unprotonated carbon; orientation is believed to depend on the stability of the incipient carbanion. (2a,b,c)

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