ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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]-CH3-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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19740570639
