Synthesis of 5- and 6-methylene-2-norbornanones-Reference-Cited by-同舟云学术

Synthesis of 5- and 6-methylene-2-norbornanones

Published:1978-04-15 Issue:8 Volume:56 Page:1134-1139
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Werstiuk Nick Henry,Taillefer Roland

Abstract

The syntheses of 4,4,6-trimethyl-5-methylene-2-norbornanone (5a), 6,6-dimethyl-2-methyl- ene-2-norbornanone (5b), 5-methylene-2-norbornanone (5c), and 6-methylene-2-norbornanone (11) are described. An unusual extended Grob-type cleavage of 6-ethylenedioxy-exo-2-methyl-endo-2-norbornanol (13d) to 2-chioroethyl (3-methyl-3-cyclopentenyl)acetate (17) is documented.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v78-191

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1. A one-step synthesis of 2-norbornanone ethylene acetals from 2-cyclopenten-1-one ethylene acetals and dienophiles via [2 + 4] cycloaddition of in situ generated 2-(2-hydroxyethoxy)cyclopenta-1,3-dienes and intramolecular reacetalization;The Journal of Organic Chemistry;1993-09

2. Reaction of cyclopent-2-en-1-one ethylene acetal with dienophiles via its ring-opened enol ether form. Single step synthesis of norbornan-2-one ethylene acetals;Journal of the Chemical Society, Chemical Communications;1991

3. Desaminierungsreaktionen, 48. Zerfall von 5‐ und 6‐Alkoxy‐2‐norbornandiazonium‐Ionen;Chemische Berichte;1988-03

4. Novel products from Beckmann fragmentation of camphor oxime in polyphosphoric acid;Tetrahedron;1988-01

5. Detection of Non-Conjugative Interactions in Rigid Cyclic Molecules by Using Carbon-13 N.M.R. Shift Values;Australian Journal of Chemistry;1987