74671-05-9Relevant academic research and scientific papers
Vinyl-Kationen, 32 Solvolysereaktionen von Cyclononinyl- und Cyclooctinylderivaten
Hanack, Michael,Spang, Werner
, p. 2015 - 2024 (2007/10/02)
5-Cyclononyn-1-yl 4-nitrobenzoate (11), 4-cyclononyn-1-yl 4-nitrobenzoate (12), and 4-cyclooctyn-1-yl 4-nitrobenzoate (13) were synthesized and their solvolysis reactions in different solvent systems were studied. 11 rearrranges on solvolysis in 50percent ethanol practically quantitatively by transanular participation of the triple bond via the vinyl cation intermediate 20 to give bicyclononan-2-one (21).On the other hand the 4-nitrobenzoates 12 and 13 solvolyse without transanular reaction, in spite of the spatial nearness between triple bond and functional C-atom.This shows that under the solvolytic conditions the strained bicyclic vinyl cations 29-32 were not formed as intermediates.
