Intramolecular addition of vinyl radicals to aldehydes

The reaction of aldehydes 1 and 10 with Bu 3SnH has been studied. In thermal conditions, after an initial chemoselective 6- exo-trig or 5- exo-trig cyclization to the aldehyde, a β-scission reaction takes place, providing rearrangement products. At low temperature, using the Et 3/O 2 procedure, sati...

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Bibliographic Details
Published in:Tetrahedron letters 1998-02, Vol.39 (8), p.833-836
Main Authors: Devin, Priscille, Fensterbank, Louis, Malacria, Max
Format: Article
Language:English
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Summary:The reaction of aldehydes 1 and 10 with Bu 3SnH has been studied. In thermal conditions, after an initial chemoselective 6- exo-trig or 5- exo-trig cyclization to the aldehyde, a β-scission reaction takes place, providing rearrangement products. At low temperature, using the Et 3/O 2 procedure, satisfactory yields of cyclohexanol 2 and cyclopentanol 11 are obtained. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10743-2