- REACTIONS DU TYPE FRIEDEL-CRAFTS DE CERTAINS ACIDES INSATURES SUR LE BENZENE XV. CONTROLE CINETIQUE DE LA REACTION DES ACIDES INSATURES CYCLIQUES
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It was studied the reaction of the cyclopentylidene- and cyclopentylacetic acids and the lactone of the cis-hydroxy-2-cyclopentaneacetic acid with the benzene in the presence of aluminium chloride complexed with nitromethane or iron(III) chloride as catalyst. In these conditions the rearrangement of the reaction products was quite limitted. The reaction products were identified and a reaction mechanism was proposed.
- Razus, Alexandru C.,Arvay, Zsolt,Birzan, Liviu,Nae, Stefania
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p. 1259 - 1266
(2007/10/03)
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- Anodic Oxidation of Norcamphor in Aqueous Electrolytes
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Norcamphor (1) was anodically oxidized at Pb/PbO2 anodes in 1 M*H2SO4, MeCN/H2O (V/V = 1/1). 3-Oxocyclopentaneacetic acid (3) and oxabicyclooctan-3-one (4) were obtained with material yields up to 76percent and 42percent, respectively.The effects of electrode materials, current densities and concentrations were studied.A possible anodic oxidation mechanism was proposed.
- Ye, Siyu,Beck, F.
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- Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXVI. The Mechanisms of Formation of the Hydration Products of 2-Norbornen-5-one
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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.
- Lajunen, Martti,Lahti, Marjo,Heimo, Satu
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p. 771 - 776
(2007/10/02)
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