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Gasphasen-Thermolyse Methyl-substituierter Bicyclo[3.2.0]hept-2-en-7-one

✍ Scribed by Peter Schiess; Peter Fünfschilling

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
629 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Gas phase thermolysis of methyl‐bicyclo [3.2.0] hept‐2‐en‐7‐ones.

Irradiation of methylnorbornenones 5a, 5b, 5c and 5e leads to the methyl‐bicyclo‐[3.2.0]hept‐2‐en‐7‐ones 4a, 4b, 4c and 4e, respectively. Upon flash thermolysis of these βγ‐unsaturated ketones dihydrotolualdehydes 9 and 10 and tolualdehydes 11 are formed as major products. The formation of these aldehydes is rationalized as involving methyl substituted ketenes 6 and conjugated heptatrienaldehydes 7 as intermediates. From the position of the methyl group in the stable pyrolysis products 9, 10 and 11 the occurrence of a thermally induced [1, 5]‐sigmatropic shift of the formyl group in 1,2‐dihydro‐tolualdehyde 8 is inferred.

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