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Automerisierung von 1,3,5,5-Tetramethylcyclohexa-1,3-dien. Vorläufige Mitteilung

✍ Scribed by Bruno C. Baumann; André S. Dreiding

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
288 KB
Volume
57
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

1,3,5,5‐Tetramethylcyclohexa‐1,3‐diene, specifically deuterated in all positions except the gem.‐dimethyl groups (11), was synthesized and found to undergo a rearrangement in the gas phase at 560°, which leads to a statistical distribution of the 6 hydrogen atoms to all 16 positions. This shows that the title compound (2) automerizes under these conditions and that the reaction proceeds via a series of ring openings (to 5) followed by degenerate [1,7]‐H‐shifts and rig closures (back to 2) rather than via [1,5]‐CH~3~‐shifts. It is suggested that the previously studied rearrangement of 5,5‐dimethylcyclohexa‐1,3‐diene (1) to 1,5‐dimethylcyclohexa‐1,3‐diene (3) takes its course by the same reaction pathway.

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