A further example of a “1,4-hydride-shift-substitution reaction”

✍ Scribed by D.W. Rome; B.L. Johnson

• Book ID: 104212448
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 105 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70790-8

✦ Synopsis

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-shift-substitution reaction (shown schematically in the aocrompanying chart) although the possibility of an intermolecular pathway was not discounted. We have ll~y found that the structurally related brcunohydrin zundergoes a similar transformation to give i.