Nechanistic aspects of thermal sigmatropic rearrangements in cycloheptatrienes have been studied extensively.2 In contrast, the synthetic potential of these isomerization reactions has been exploited only recently. For example, a facile entry to tricyclo[4.3.1.03g8]decane (protoadamantane) derivativ
Multiple thermal rearrangements. Pyrolysis of 7-allyloxycycloheptatriene
β Scribed by Cupas, Chris A.; Schumann, William.; Heyd, William E.
- Book ID
- 127344690
- Publisher
- American Chemical Society
- Year
- 1970
- Tongue
- English
- Weight
- 375 KB
- Volume
- 92
- Category
- Article
- ISSN
- 0002-7863
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In previous studies we have shown that the thermal rearrangement of appropriately substituded cycloheptatrienes and dihydrotropones provides a facile synthetic entry to new bridged polycyclic systems. For example, pyrolysis of 7-allyloxycycloheptatriene (lJ produces, in high yield, equal amounts of
## Abstract Flash vacuum pyrolysis of 1,2βdialkoxybenzenes 1aβc leads to the liberation of alkanes from the interacting side chains. A rearrangement of the skeleton yields the __o__βhydroxy carbonyl compounds 2 and 4. The generation of phenol 3 can be rationalized by a decarbonylation. The latter r