A new reaction of diazomethane with norbornyl α-diketones

Faiz Ahmed Khan, Rashmirekha Satapathy, Ch Sudheer, Ch Nageswara Rao

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Abstract

A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d4-MeOH, EtOH and d6-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d 4-18 and diazomethane in the presence of d4-MeOH as solvent.

Original languageEnglish (US)
Pages (from-to)7193-7196
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number42
DOIs
StatePublished - Oct 17 2005

Bibliographical note

Funding Information:
This work was supported by the Department of Science and Technology (DST), New Delhi. F.A.K. acknowledges the DST for a Swarnajayanti Fellowship. R.S., C.S. and C.N.R. thank CSIR/UGC for fellowships.

Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.

Keywords

  • Diazomethane
  • Ketal
  • Oxiranes
  • Regioselectivity
  • α-Diketones

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