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Aerobic oxidation of various alcohols has been accomplished by using a new catalytic system, N-hydroxyphthalimide (NHPI) combined with Co (acac). A practical catalytic method to convert alkylbenzenes into the corresponding carboxylic acids under atmospheric dioxygen at ambient temperature using a combined catalytic system consisting of N-hydroxyphthalimide (NHPI) and Co (OAc) 2 was developed. Novel catalysis by N-hydroxyphthalimide in the oxidation of organic substrates by molecular oxygen was described. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Purely organic and catalytic systems of anthraquinones and N-hydroxyphthalimide efficiently promote oxygenation of hydrocarbons with dioxygen under mild conditions. Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with was transition metal salts.
Yasutaka Ishii,; Takahiro Iwahama,; Satoshi Sakaguchi,; Kouichi Nakayama,; Yutaka Nishiyama. Alkane Oxidation with Molecular Oxygen Using a New Efficient Catalytic System:? N-Hydroxyphthalimide (NHPI) Combined with Co(acac)n (n = 2 or 3). J. Org. Chem., 1996, 61 (14), 4520-4526.
Yasushi Yoshino,; Yoshiaki Hayashi,; Takahiro Iwahama,; Satoshi Sakaguchi,; Yasutaka Ishii. Catalytic Oxidation of Alkylbenzenes with Molecular Oxygen under Normal Pressure and Temperature by N-Hydroxyphthalimide Combined with Co(OAc)2. J. Org. Chem. 1997, 62 (20), 6810-6813.
Additive in the carbodiimide method of peptide coupling, leading to decreased racemization: J. Am. Chem. Soc., 89, 7151 (1967). For alternative reagents, see N,N'-Dicyclohexylcarbodiimide, A10973, and Appendix 6.
O-Alkylation followed by hydrazinolysis gives O-alkylhydroxylamines: Bull. Soc. Chim. Fr., 833 (1976). Copper-promoted coupling with arylboronic acids, followed by hydrazinolysis, affords O-arylhydroxylamines: Org. Lett., 3, 139 (2001).
Efficient electron carrier for electrochemical oxidation of alcohols: J. Chem. Soc., Chem. Commun., 479 (1983). Has also been found to be an efficient catalyst for non-electrochemical oxidation of benzylic groups in benzonitrile solution with atmospheric pressure oxygen: J. Org. Chem., 60, 3934 (1995). The method can be extended to alkanes by the use of a catalyst such as 0.5-1 mol% Co(acac)2. Thus cyclohexane is oxidized to cyclohexanone and adipic acid; adamantane gives mainly 1-adamantanol with minor amounts of 2-adamantanone and 1,3-adamantanediol: J. Org. Chem., 61, 4520 (1996). Under similar conditions alkynes can be oxygenated to ɑß-acetylenic ketones in good yields: Chem. Commun., 2037 (1998).
Mentions de danger (UE): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Mentions de prudence: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.