Abstract:
Carbonylation of n-octyl acetate in the presence of CBr4·2AlBr3 followed by treatment with nucleophiles such as alcohols, amines or (het)arenes affords 7-acetoxy-2,2-dimethylheptanoyl-containing products.
Citation:
I. S. Akhrem, D. V. Avetisyan, L. V. Afanas'eva, A. V. Orlinkov, N. D. Kagramanov, P. V. Petrovskii, “Superelectrophilic sp3 C–H carbonylation of n-octyl acetate as a way to new bifunctional neo-octanes”, Mendeleev Commun., 21:6 (2011), 323–325
Linking options:
https://www.mathnet.ru/eng/mendc2959
https://www.mathnet.ru/eng/mendc/v21/i6/p323
This publication is cited in the following 12 articles:
Ana M. Faisca Phillips, Armando J. L. Pombeiro, Alkane Functionalization, 2019, 371
I. S. Akhrem, D. V. Avetisyan, L. V. Afanas'eva, A. A. Tyutyunov, O. I. Artyushin, N. D. Kagramanov, “Regioselective functionalization of gem-bis(trifluoromethylated) alkanols”, Mendeleev Commun., 28:6 (2018), 651–652
Yurii A. Borisov, Irena S. Akhrem, “DFT mechanistic study of reactions of S6H6 and 1,3,5-Ad3C6H3 with CBr3. The first example of hydride transfer from aromatic C H bond to electrophile”, Journal of Molecular Catalysis A: Chemical, 426 (2017), 610
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Oleg I. Artyushin, Nikolai D. Kagramanov, Andrey L. Sigan, “A new method of one-pot synthesis of dicarboxylic acid derivatives and diketones containing quaternary carbon atom and remote functional groups from linear acyl halides”, Tetrahedron Letters, 58:42 (2017), 4014
Irena S. Akhrem, Djul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Oleg I. Artushin, Nikolai D. Kagramanov, “Superelectrophilic sp 3 C H bond intermolecular functionalization of primary alcohols C n H 2 n +1 OH ( n = 7, 8, 9) leading to new neo-alcohols with remote functional groups or new macrocyclic lactides”, Tetrahedron Letters, 57:17 (2016), 1863
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Oleg I. Artyushin, Nikolai D. Kagramanov, “Intermolecular sp 3 C–H bond functionalization of alkyl amides as a new method for the one-pot synthesis of functional neo alkyl amides with remote functional groups”, Tetrahedron Letters, 56:3 (2015), 562
Irena S. Akhrem, “Recent achievements in intermolecular sp3 C–H bond functionalization of organic compounds by superelectrophilic trihalomethyl metal complex”, Journal of Organometallic Chemistry, 793 (2015), 54
I. S. Akhrem, L. V. Afanas'eva, I. M. Churilova, O. I. Artyushin, N. D. Kagramanov, “Chemo- and regioselective remote functionalization of nonanamides via sp3 C–H bond cleavage under superelectrophilic conditions”, Mendeleev Commun., 25:2 (2015), 124–125
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Irina M. Churilova, Lyudmila V. Afanas'eva, Oleg I. Artyushin, Nikolai D. Kagramanov, “Intermolecular sp3 C–H bond functionalization of alkyl alkanoates as a new method for the one-pot synthesis of functional neo alkyl alkanoates with remote functional groups”, Tetrahedron Letters, 54:45 (2013), 6037
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Alexander V. Orlinkov, Nikolai D. Kagramanov, Pavel V. Petrovskii, “ChemInform Abstract: Superelectrophilic sp3 C—H Carbonylation of n‐Octyl Acetate as a Way to New Bifunctional neo‐Octanes.”, ChemInform, 43:16 (2012)
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Luidmila V. Afanas'eva, “The first selective one-pot synthesis of 1,3-dicarbonyl adamantanes from adamantane and 1,3-dimethyladamantane”, Tetrahedron Letters, 53:27 (2012), 3493
Irena S. Akhrem, Lyudmila V. Afanas'eva, Nikolai D. Kagramanov, Pavel V. Petrovskii, “sp3 C–H bond functionalization of methyl n-alkyl ketones [MeCOCnH2n+1 (n=6–8)] as a novel method for the one-pot regioselective synthesis of 'bifunctional alkanes' with remote functional groups”, Tetrahedron Letters, 53:32 (2012), 4221
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