Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose
Oxidations of D-glucono-1,5-lactone, D-glucono-1,4-lactone, calcium D-gluconate, and 3-deoxy-D-arabinohexono-1,4-lactone by cerium(IV) sulphate in sulphuric acid were studied at 25 and at 37 °C, with various concentrations of reactants and acidities. The results indicated that it is the aldonic acid...
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todo:paper_1472779X_v_n5_p685_Sala2023-10-03T16:18:02Z Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose Sala, L.F. Cirelli, A.F. De Lederkremer, R.M. Oxidations of D-glucono-1,5-lactone, D-glucono-1,4-lactone, calcium D-gluconate, and 3-deoxy-D-arabinohexono-1,4-lactone by cerium(IV) sulphate in sulphuric acid were studied at 25 and at 37 °C, with various concentrations of reactants and acidities. The results indicated that it is the aldonic acid that undergoes oxidation ; the stoicheiometry requires two cerium(IV) ions for the oxidation of one molecule of aldonic acid to the next lower sugar. The rate of disappearance of cerium(IV) ions depended directly on its concentration, but the dependence on the organic substrate concentration suggested the existence of an intermediate complex; this was proved by a spectrophotometric method. The complex undergoes slow unimolecular decomposition to a free radical, which reacts with CeIV to afford the products. The reaction rate was proportional to 1/[SO<inf>4</inf>H<inf>2</inf>]2. A preparative experiment with D-glucono-1.5-lactone gave crystalline D-arabinose in 94% yield. Fil:Sala, L.F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1472779X_v_n5_p685_Sala |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
Oxidations of D-glucono-1,5-lactone, D-glucono-1,4-lactone, calcium D-gluconate, and 3-deoxy-D-arabinohexono-1,4-lactone by cerium(IV) sulphate in sulphuric acid were studied at 25 and at 37 °C, with various concentrations of reactants and acidities. The results indicated that it is the aldonic acid that undergoes oxidation ; the stoicheiometry requires two cerium(IV) ions for the oxidation of one molecule of aldonic acid to the next lower sugar. The rate of disappearance of cerium(IV) ions depended directly on its concentration, but the dependence on the organic substrate concentration suggested the existence of an intermediate complex; this was proved by a spectrophotometric method. The complex undergoes slow unimolecular decomposition to a free radical, which reacts with CeIV to afford the products. The reaction rate was proportional to 1/[SO<inf>4</inf>H<inf>2</inf>]2. A preparative experiment with D-glucono-1.5-lactone gave crystalline D-arabinose in 94% yield. |
| format |
JOUR |
| author |
Sala, L.F. Cirelli, A.F. De Lederkremer, R.M. |
| spellingShingle |
Sala, L.F. Cirelli, A.F. De Lederkremer, R.M. Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| author_facet |
Sala, L.F. Cirelli, A.F. De Lederkremer, R.M. |
| author_sort |
Sala, L.F. |
| title |
Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| title_short |
Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| title_full |
Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| title_fullStr |
Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| title_full_unstemmed |
Oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; Synthesis of d-arabinose |
| title_sort |
oxidative decarboxylation of aldonolactones by cerium(iv) sulphate in aqueous sulphuric acid; synthesis of d-arabinose |
| url |
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n5_p685_Sala |
| work_keys_str_mv |
AT salalf oxidativedecarboxylationofaldonolactonesbyceriumivsulphateinaqueoussulphuricacidsynthesisofdarabinose AT cirelliaf oxidativedecarboxylationofaldonolactonesbyceriumivsulphateinaqueoussulphuricacidsynthesisofdarabinose AT delederkremerrm oxidativedecarboxylationofaldonolactonesbyceriumivsulphateinaqueoussulphuricacidsynthesisofdarabinose |
| _version_ |
1807324137351282688 |