A FACILE ROUTE TO MACROCYCLIC KETONES. DIRECT DIVINYLATION OF 2-CHLOROCYCLODODECAN-1-ONE
- 5 July 1973
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 2 (7) , 667-670
- https://doi.org/10.1246/cl.1973.667
Abstract
The reaction of 2-chlorocyclododecan-1-one with vinylmagnesium chloride (molar ratio at 1:2) gave directly 1,2-divinylcyclododecan-1-ol, which was easily converted to 5-cyclohexadecen-1-one. This one-step divinylation was found to proceed not through a direct displacement of the Grignard reagent with the chlorine atom, but through a pinacol-like rearrangement of a vinyl group.Keywords
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