Anti-Markovnikov addition to alkenes with a neighbouring thioacetal function

The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition. The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readditi...

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 27; pp. 4549 - 4551
Main Authors Bongardt, Tim, Dreeßen, Sylvia, Tiedemann, Ralf, Schaumann, Ernst
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.07.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclisation
Markovnikov rule
Physical Sciences
Pyrans
Regioselectivity
Science & Technology
Tetrahydrofurans
Markovnikov rule
Cyclisation
Regioselectivity
Tetrahydrofurans
Pyrans
regioselectivity
pyrans
SYNTHETIC ROUTES
tetrahydrofurans
cyclisation
RULES
INDUCED CYCLIZATIONS
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Summary:The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition. The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readdition.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.05.009