Preparation of Carboxylic Acids Part 4 Oxidation of Alkenes and Arenes

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This video is about the preparation of carboxylic acids by oxidation of alkenes and arenes. You'll find examples of oxidations with hydrogen peroxide, tert-butylhydroperoxide, periodate, oxone, nitric acid, chlorate, hypochlorite, ozone, and permanganate. At the end of the video there are some examples of the more critical potential side reactions. • Further examples (patents are available at https://worldwide.espacenet.com/) • Org. Syn. 1996, 73, 215 (alkene, H2CrO4); 1988, 66, 180 (catechol, O2, Cu); 1986, 64, 150 (O3); 1981, 60, 11 (alkene, KMnO4); 1958, 38, 32 (arene, O3); 1954, 34, 8 (2-naphthol, MeCO3H); 1950, 30, 86 (arene, KMnO4); 1949, 29, 49 (alkene, K2Cr2O7); 1944, 24, 38 (alkene, CrO3); 1936, 16, 68 (naphthalene, KMnO4); • Org. Lett. 2023, 25, 293-297 (alkyne); J. Am. Chem. Soc. 2022, 144, 15437-15442 (alkene, ArNO2); Org. Biomol. Chem. 2022, 20, 5452-5462 (arene, NaIO4); J. Org. Chem. 2022, 87, 13573-13582 (arene, OsO4); 2021, 86, 14974-14982 (alkene, O2); Org. Chem. Front. 2021, 8, 3102-3109 (alkene, O2); J. Am. Chem. Soc. 2021, 143, 10005-10013 (O2, Mn); 2020, 142, 10125-10131 (arene); Org. Lett. 2020, 22, 5279-5283 (furan, NaIO4); J. Org. Chem. 2020, 85, 6159-6164 (arene, H2O2); 3728-3741 (styrenes, tBuOOH); ACS Catal. 2019, 9, 671-678; 2018, 8, 10173-10179 (arene dimerization); 2017, 7, 3050-3060 (alkenes, review); J. Org. Chem. 2017, 82, 9342-9349 (alkene, H2O2); 2014, 79, 8906-8911 (arene, H2O2); Tetrahedron 2013, 69, 3817-3822 (arene, NaIO4); J. Org. Chem. 2012, 77, 96-107 (NaIO4); Tetrahedron Lett. 2010, 51, 3123-3126 (alkene, NaIO4); Org. Proc. Res. Dev. 2010, 14, 252-258 (alkene, H2O2); Org. Lett. 2010, 12, 5640-5643 (alkene, oxone); 1552-1555 (alkene, NMO, PhI(OAc)2, Os); 2007, 9, 2469-2472 (alkyne, NaIO4); 2006, 8, 693-696 (alkene, tBuOOH); Org. Proc. Res. Dev. 2006, 10, 941-943 (styrene); J. Mol. Catal. Chem. 2003, 195, 139-145 (electrogenerated NaIO4); Electrochim. Acta 2003, 48, 489-495; J. Am. Chem. Soc. 2002, 124, 3824-3825 (alkene, oxone, Os); J. Org. Chem. 2002, 67, 8079-8085 (polyene); 2001, 66, 4504-4510 (alkene); Bull. Chem. Soc. Jpn. 1995, 68, 2989-2992 (HIO4); J. Org. Chem. 1990, 55, 1928-1932 (HIO4).

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