The Molecularity of the Newman− Kwart Rearrangement

M Burns, GC Lloyd-Jones, JD Moseley…

Index: Burns, Matthew; Lloyd-Jones, Guy C.; Moseley, Jonathan D.; Renny, Joseph S. Journal of Organic Chemistry, 2010 , vol. 75, # 19 p. 6347 - 6353

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Citation Number: 19

Abstract

It was recently reported that the venerable Newman− Kwart rearrangement (1→ 2) proceeds via mixed first-and second-order kinetics. Prior to this, the rearrangement had been considered to proceed exclusively via an intramolecular OAr→ SAr migration. A new bimolecular pathway, possibly involving an 8-membered cyclic transition state, was proposed to account for reaction rates that increased disproportionately with substrate ...

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