Novel generation of (α-ketovinyl)thioketenes as intermediates through tandem [2,3]/[3,3] sigmatropic rearrangement of alkynyl propargyl sulfoxides

Thermal reaction of alkynyl propargyl sulfoxides 1 afforded novel highly reactive (α-ketovinyl)thioketenes 3. Trapping experiments using a primary or secondary amine, formation of furanophane 4, through head-to-tail type dimerization, as well as direct observation using 1H NMR elucidated the generat...

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Bibliographic Details
Published in:Tetrahedron letters 2007-06, Vol.48 (26), p.4639-4642
Main Authors: Aoyagi, Shigenobu, Makabe, Muneyoshi, Shimada, Kazuaki, Takikawa, Yuji, Kabuto, Chizuko
Format: Article
Language:English
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Summary:Thermal reaction of alkynyl propargyl sulfoxides 1 afforded novel highly reactive (α-ketovinyl)thioketenes 3. Trapping experiments using a primary or secondary amine, formation of furanophane 4, through head-to-tail type dimerization, as well as direct observation using 1H NMR elucidated the generation pathway of 3 through sequential [2,3]/[3,3] sigmatropic rearrangement.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.04.055