Džonsova oksidacija

Džonsova oksidacija (engl. Jones oxidation) je hemijska reakcija opisana kao oksidacija hromnom kiselinom primarnih i sekundarnih alkohola u karboksilne kiseline i ketone, respektivno.^[1]^[2]^[3]^[4]^[5]^[6]^[7] Džonsov reagens - rastvor hrom trioksida u koncentrovanoj sumpornoj kiselini – se koristi kao oksidaciono sredstvo.

Džonsov reagens takođe kompletno oksiduje aldehide u karboksilne kiseline.

Rastvarač aceton ima primetnog uticaja na osobine hromne kiseline. Oksidacija je veoma brza, egzotermna, i prinosi su tipično visoki. Ovaj reagens retko oksiduje nezasićene veze.

Hromijum ostatak je veoma toksičan, i mora se obratiti pažnja da je uklonjen na korektan način.

Reference

^ Bowden, K.; Heilbron, I. M.; Jones, E. R. H (1946). „13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols”. J. Chem. Soc.: 39. doi:10.1039/jr9460000039.
^ Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F (1949). „129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols”. J. Chem. Soc.: 604. doi:10.1039/jr9490000604.
^ Bladon, P; Fabian, Joyce M.; Henbest, H. B.; Koch, H. P.; Wood, Geoffrey W. (1951). „532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres”. J. Chem. Soc.: 2402. doi:10.1039/jr9510002402.
^ Jones, E. R. H (1953). „92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A”. J. Chem. Soc.: 457. doi:10.1039/jr9530000457.
^ Jones, E. R. H (1953). „520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C”. J. Chem. Soc.: 2548. doi:10.1039/jr9530002548.
^ Jones, E. R. H (1953). „599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A”. J. Chem. Soc.: 3019. doi:10.1039/jr9530003019.
^ C. Djerassi, R. Engle & A. Bowers (1956). „Notes - The Direct Conversion of Steroidal Δ5-3β-Alcohols to Δ5- and Δ4-3-Ketones”. J. Org. Chem. 21 (12): 1547—1549. doi:10.1021/jo01118a627.

Literatura

E. J. Eisenbraun (1973). „Cyclooctanone”. Org. Synth. ; Coll. Vol., 5, стр. 310
J. Meinwald; J. Crandall; W. E. Hymans (1973). „Nortricyclanone”. Org. Synth. ; Coll. Vol., 5, стр. 866
Bowden, K.; Heilbron, I. M.; Jones, E. R. H (1946). „13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols”. J. Chem. Soc.: 39. doi:10.1039/jr9460000039.
Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F (1949). „129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols”. J. Chem. Soc.: 604. doi:10.1039/jr9490000604.
Bladon, P; Fabian, Joyce M.; Henbest, H. B.; Koch, H. P.; Wood, Geoffrey W. (1951). „532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres”. J. Chem. Soc.: 2402. doi:10.1039/jr9510002402.
Jones, E. R. H (1953). „92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A”. J. Chem. Soc.: 457. doi:10.1039/jr9530000457.
Jones, E. R. H (1953). „520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C”. J. Chem. Soc.: 2548. doi:10.1039/jr9530002548.
Jones, E. R. H (1953). „599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A”. J. Chem. Soc.: 3019. doi:10.1039/jr9530003019.
C. Djerassi; R. Engle; A. Bowers (1956). „Notes – The Direct Conversion of Steroidal Δ5-3β-Alcohols to Δ5- and Δ4-3-Ketones”. J. Org. Chem. 21 (12): 1547—1549. doi:10.1021/jo01118a627.

[1] Bowden, K.; Heilbron, I. M.; Jones, E. R. H (1946). „13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols”. J. Chem. Soc.: 39. doi:10.1039/jr9460000039.

[2] Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F (1949). „129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols”. J. Chem. Soc.: 604. doi:10.1039/jr9490000604.

[3] Bladon, P; Fabian, Joyce M.; Henbest, H. B.; Koch, H. P.; Wood, Geoffrey W. (1951). „532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres”. J. Chem. Soc.: 2402. doi:10.1039/jr9510002402.

[4] Jones, E. R. H (1953). „92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A”. J. Chem. Soc.: 457. doi:10.1039/jr9530000457.

[5] Jones, E. R. H (1953). „520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C”. J. Chem. Soc.: 2548. doi:10.1039/jr9530002548.

[6] Jones, E. R. H (1953). „599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A”. J. Chem. Soc.: 3019. doi:10.1039/jr9530003019.

[7] C. Djerassi, R. Engle & A. Bowers (1956). „Notes - The Direct Conversion of Steroidal Δ5-3β-Alcohols to Δ5- and Δ4-3-Ketones”. J. Org. Chem. 21 (12): 1547—1549. doi:10.1021/jo01118a627.

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