Acid-catalyzed isomerization of 1-halo-2-arylthioalk-1-enesстатья
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Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
Аннотация:1-Halo-2-arylthioalk-1-enes, the anti-Markovnikov adducts of 1,2-halosulfenylation of terminal alkynes containing propargyl hydrogen atoms, were found to transform into a mixture of E- and Z-isomers of 1-halo-2-arylthioalk-2-enes under acid catalysis conditions. A plausible mechanism of rearrangement is proposed. The Markovnikov adducts 2-halo-1-arylthioalk-1-enes were partially converted into their cis-form under similar conditions. The halosulfenylation products of 1-phenylpent-1-yne did not show the signs of double-bond migration in the presence of an acid; only partial isomerization of the E- to the Z-isomers took place.