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A base-induced transannular 1,4-hydride shift in a cyclohexanone

✍ Scribed by Warnhoff, E. W.

Book ID
120981642
Publisher
The Royal Society of Chemistry
Year
1976
Tongue
English
Weight
133 KB
Volume
13
Category
Article
ISSN
0022-4936

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πŸ“œ SIMILAR VOLUMES

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Gwynn and Skillern' have reoently noted that basic treatment of a-6&rcmomethylnorbornanexo-2-01 I aan give rise to ketone 2 depending on basis conditions. For example, NaB/TBF reacts with I to yield 2 almost exclusively. This conversion was rationalised in terms of a novel intramolecular l,Chydride-

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Upon treatment with Nail in DMF the homoallylic ethers lag and the amine lh undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of la and lb show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mo