Acid-Catalyzed Isomerization of 1-Halo-2-Arylthioalk-1-Enes

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 rearrangem...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2002-03, Vol.177 (3), p.555-565
Main Authors: Zyk, Nikolai V., Beloglazkina, Elena K., Belova, Maria A., Zatonsky, Stanislav V., Zefirov, Nikolai S.
Format: Article
Language:English
Subjects:
1-halo-2-arylthioalk-1-enes
1-halo-2-arylthioalk-2-enes
Acid Catalysis
Isomerization
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Summary: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.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500210267