58029-22-4Relevant academic research and scientific papers
Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXVI. The Mechanisms of Formation of the Hydration Products of 2-Norbornen-5-one
Lajunen, Martti,Lahti, Marjo,Heimo, Satu
, p. 771 - 776 (2007/10/02)
The acid-catalyzed hydration of 2-norbornen-5-one (1) in 5 mol dm-3 HClO4 at 358 K produces, according to GLC analyses, exo-5-hydroxy-2-norbornanone (2), 2-oxabicycloctan-3-one (3), which is in equilibrium with cis-3-hydroxycyclopentaneacetic acid (5), and 2-oxabicyclooctan-3-one (4).The former lactone (3) is unstable and rearranges slowly to the latter (4).The ketoalcohol (2) is formed via the slow protonation of norbornenone at C(3) and via subsequent hydration of the carbocation.The lactones are formed via complicated routes started by the protonation of norbornenone at C(2), and comprising 3- and 2-cyclopentaneacetic acid (7 and 9) as unstable intermediate products.
