34029-61-3Relevant academic research and scientific papers
ADDITION OF ACETIC ACID TO 2-VINYLBICYCLOHEPTANE, 5-VINYLBICYCLOHEPT-2-ENE, AND 1-VINYLTRICYCLO2,6>-HEPTANE
Bobyleva, A. A.,Belikova, N. A.,Kalinichenko, A. N.,Baryshnikov, A. T.,Dubitskaya, N. F.,et al.
, p. 1397 - 1403 (2007/10/02)
The addition of acetic acid to 2-vinylbicycloheptane, 5-vinylbicyclohept-2-ene, and 1-vinyltricyclo2,6>heptane was investigated, and the reaction rate constants were determined.The main direction in the transformations of the former is ring enlargement and the formation of acetates of the bicyclooctane series.Direct addition of the nucleophile and hydride shift with subsequent Wagner-Meerwein rearrangement occur to a lesser degree.The addition of acetic acid to 5-vinylbicyclohept-2-ene occurs exclusively at the intracyclic double bond; the effect of the stereochemical orientation of the vinyl group on the direction of the reaction was investigated.With acetic acid 1-vinyltricyclo2,6>heptane gives 1,4-addition products, i.e., acetates of E- and Z-6-ethylidenebicycloheptan-exo-2-ols; the 1,2-addition product, i.e., the acetate of 1-(α-hydroxyethyl)tricyclo2,6>heptane, is formed intermediately.
