Abstract:
Treatment of 1-bromoadamantane and 1-bromo-3,5-dimethyladamantane with CBr4·2AlBr3 under carbon monoxide atmosphere followed by quenching with nucleophiles affords 1,3-dicarbonyl adamantanes.
Citation:
I. S. Akhrem, D. V. Avetisyan, L. V. Afanas'eva, E. I. Goryunov, I. M. Churilova, P. V. Petrovskii, N. D. Kagramanov, “The first one-pot synthesis of 1,3-dicarbonyl adamantanes from 1-bromoadamantanes”, Mendeleev Commun., 21:5 (2011), 259–261
Linking options:
https://www.mathnet.ru/eng/mendc2936
https://www.mathnet.ru/eng/mendc/v21/i5/p259
This publication is cited in the following 11 articles:
E. A. Ivleva, D. V. Zvereva, Yu. N. Klimochkin, “New Features of the H2SO4–HNO3 System in the Synthesis of Adamantanecarboxylic Acids”, Russ J Gen Chem, 94:8 (2024), 1905
Ana M. Faisca Phillips, Armando J. L. Pombeiro, Alkane Functionalization, 2019, 371
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
Maxime Grillaud, Alberto Bianco, “Multifunctional adamantane derivatives as new scaffolds for the multipresentation of bioactive peptides”, Journal of Peptide Science, 21:5 (2015), 330
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, Dzhuletta V. Avetisyan, Lyudmila V. Afanas'eva, Evgenii I. Goryunov, Irina M. Churilova, Pavel V. Petrovskii, Nikolai D. Kagramanov, “ChemInform Abstract: The First One‐Pot Synthesis of 1,3‐Dicarbonyl Adamantanes from 1‐Bromoadamantanes.”, ChemInform, 43:10 (2012)
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