Mechanism of thermal rearrangement of the spiro bicyclo[2.1.0]-pentane-5,2′-methylenecyclopropanes to 6- and 7- methylenebicyclo[3.2.0]hept-1-enes
AUTOR(ES)
Lokensgard, David M.
RESUMO
The thermal rearrangements of the bicyclo[2.1.0]pentane-5,2′-methylenecyclopropanes fall into two classes. The first occurs near 80°C and consists of a double epimerization (“bridge flip”) which is initiated by cleavage of the bridge bond. An alternative mechanism by way of a trimethylenemethane intermediate is ruled out by an isotopic position-marking experiment. The second rearrangement begins to be detected above 120°C. It gives the isomeric 6- and 7-methylenebicyclo[3.2.0]hept-1-enes. Two possible mechanisms can operate in this complex change, but a choice between them is not yet possible.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=349557Documentos Relacionados
- Benzoate catalysis in the hydrolysis of endo-5-[4′(5′)imidazolyl]-bicyclo[2.2.1]hept-endo- 2-yl trans-cinnamate: Implications for the charge-transfer mechanism of catalysis by serine proteases
- Computational study on structure and properties of new energetic material 3,7-bis(dinitromethylene)-2,4,6,8-tetranitro-2,4,6,8-tetraaza-bicyclo[3.3.0]octane
- Estudo de reatividade e resolução enantiomérica do (+-)-10-exo-hidróxipentaciclo[6.2.1.1 3,6.0 2,7. 0 5.9] dodecan-4-ona
- Electrochemical hydrogen-storage properties of La0.78Mg0.22Ni2.67Mn0.11Al0.11Co0.52-M1Ni3.5Co0.6Mn0.4Al0.5 composites
- Sintese de pirrolizidinas ariladas : estudo da regiosseletividade da reação de Baeyer-Villiger das 7-(Alquil)-2-Azabiciclo[3.2.0]-Pentan-6-Ona