Issue 13, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Ritter reactions. Part 14.1 Rearrangement of 3,3,7,7-tetramethyl-6-methylidenebicyclo[3.3.1]nonan-2-one

Djamal Djaidi,a   Ivy S. H. Leung,a   Roger Bishop,*a   Donald C. Craiga  and  Marcia L. Scuddera  

* Corresponding authors

a School of Chemistry, The University of New South Wales, UNSW SYDNEY, Australia

Abstract

When the bicyclic ketone 1 is reacted with concentrated sulfuric acid and acetonitrile a complex sequence of reactions ensues. The compounds 2–6 are formed, with several of these being obtainable in good yields through careful control of the reaction conditions. X-Ray crystallography was used to determine unambiguously the structures of 4–6. These molecular conversions involve both rearrangement and Ritter reactions, and mechanistic explanations are proposed.

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Article information

DOI
https://doi.org/10.1039/B002544P
Article type
Paper
Submitted
30 Mar 2000
Accepted
03 May 2000
First published
09 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2037-2042

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Ritter reactions. Part 14. Rearrangement of 3,3,7,7-tetramethyl-6-methylidenebicyclo[3.3.1]nonan-2-one

D. Djaidi, I. S. H. Leung, R. Bishop, D. C. Craig and M. L. Scudder, J. Chem. Soc., Perkin Trans. 1, 2000, 2037 DOI: 10.1039/B002544P

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