The dispiroketones 46 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the [3.3.3]propellane 37 under thermodynamic control. The corresponding alcohols 10-12 all yield the [3.3.3]propeUane 41. The rearrangement of [7,7-D2)-12 to [8
Synthesis and rearrangement of functionalized dispiro [3.0.3.3]Undecanes - a new entry to [3.3.3]Propellanes1
β Scribed by Lutz Fitjer; Andreas Kanschik; Marita Majewski
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 230 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
## Abstract Formation of (β)β[4.3.3]propellane 4 from (β)β14βhydroxymodhephene (2) proceeds through a WagnerβMeerwein rearrangement via C3ο£ΏC4 bondβshift to give a stable intermediate, dimethylcyclohexadienyl cation A, which undergoes deprotonation. Herein, this mechanism was investigated by using a
## Abstract The unusual propellane skeleton of the sesquiterpene modhephene (**1**) has been synthesized starting from cyclopentenone (**2**). The key step **6** β **7** is an efficient and highly stereoselective intramolecular thermal eneβreaction. Further elaboration of the propellane **7** gave