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Stereospecific Synthesis of 1,2-Difunctionalized Buta-1,3-Dienes via Tandem [3,3]–[3,3] Sigmatropic Rearrangements

✍ Scribed by Klaus Banert; Jana Schlott

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 136 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00459-2

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✦ Synopsis

AbstractÐThermolysis of bis-thiocarbamates derived from but-3-yne-1,2-diols resulted in the formation of buta-1,3-dienes with carbamoylthio groups in positions 1 and 2 with good to excellent yields. The stereochemistry of the products is controlled by substituents at C-1 of the starting material and can be explained by chair-like reacting conformations.

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