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A new reaction of diazomethane with norbornyl α-diketones
, R. Satapathy, Ch. Sudheer, Ch.N. Rao
Published in
2005
Volume: 46
   
Issue: 42
Pages: 7193 - 7196
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.
About the journal
JournalTetrahedron Letters
ISSN00404039