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- Title
2- und 6-Methyl-8-oxa-bicyclo[5.1.0]octa-2,4-dien. Über den Verlauf der Ringöffnung bei der Thermolyse in der Gasphase.
- Authors
Schiess, Peter; Fünfschilling, Peter
- Abstract
2- and 6-Methyl-8-oxabicyclo[5.1.0]octa-2,4-diene. Ring cleavage reaction upon flash pyrolysis. 6-Methyl-8-oxa-bicyclo[5.1.0]-octa-2,4-diene ( 1 a) has been subjected to flash pyrolysis with the aim to elucidate the course of its thermal ring cleavage reaction. At 100° equilibrium between 1a (6%) and its 2-methylisomer 1 b (94%) is reached through a remarkably facile [1,5]-hydrogen shift. Above 200° methyl-bicyclo[3.2.0]hept-2-ene-7-ones ( 3), dihydrotolualdehydes 5 and 6 and their aromatization products 7 are isolated. It is concluded that these products arise from 2-, 3- and 7-methyl-hepta-2,4,6-trienal 2a, 2b and 2f which are formed from 1a/1b by path C and D in Scheme 2 involving a formal [2+6]-cycloreversion reaction of 1a/1b and of its valence isomer, 1,2-homooxepine 11. Two alternate pathways, A and B, involving cleavage of the C,C bond common to both rings in 1 concomitant or followed by hydrogen shifts are not operative.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 5, p1756
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590534