- Reactions of quino-ketenes with C-Nucleophiles: Syntheses of (2-Hydroxyphenyl)methanols and 2-Hydroxyphenyl Ketones
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In this study, we have developed a new, efficient, and one-step protocol for the synthesis of derivatives of 2,4-dihydroxyphenyl ketones and/or 2,4-dihydroxyphenyl/naphthalenyl methanols starting from benzodioxinones/ naphthodioxinones and organolithium compounds. Reactions have been performed under thermal conditions without catalyst. This work is the first example of the preparation of these products starting from 2-hydroxy acids. Copyright
- Guenduez, Hande,Kumbaraci, Volkan,Talinli, Naciye
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- Nucleophilic addition reaction with dearomatization of naphthalene ring
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Various aromatic lactones have been synthesized and their regioselectivity (1,2-addition vs. 1,4- or 1,6-addition) investigated in reactions with organolithium species, particularly n-BuLi and sec-BuLi. The regioselectivity varied greatly depending on various factors, such as the bulkiness of both substrates and organolithium species, and types of solvent and cosolvent. In particular, 1,4-addition with dearomatization occurred preferentially using sec-BuLi as the nucleophile in tetrahydrofuran (THF) with hexamethylphosphoramide (HMPA) or N,N′-dimethylpropyleneurea (DMPU) as cosolvent. For sec-BuLi, the reaction was estimated to proceed through a single-electron transfer mechanism.
- Imayoshi, Ayumi,Kiyotaki, Kotaro,Sasaki, Hirotaka,Tsubaki, Kazunori
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p. 384 - 391
(2020/05/14)
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- NaHSO4/SiO2catalyzed generation of: o -quinone/ o -thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization
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ortho-Quinone methides, very reactive transient intermediates, are utilized successfully in synthesizing complex organic molecules of natural and biological significance. Among several synthetic protocols, the acid catalyzed generation of ortho-quinone me
- Anthony, Savarimuthu Philip,Karthick, Muthupandi,Konikkara Abi, Edwin,Ramanathan, Chinnasamy Ramaraj,Someshwar, Nagamalla
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p. 8653 - 8667
(2020/11/17)
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- Desymmetrization of Symmetrical Triarylcarbinols: Synthesis of 7-Arylfluorenes and a C 2 -Symmetric Chiral BIFOL Phosphoric Acid
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A simple and an efficient method for the synthesis of 7-arylfluorenes by intramolecular cyclization of the corresponding triarylcarbinols in the presence of the solid-acid catalyst NaHSO 4 /SiO 2 has been developed. By using this method, a new chiral diol with a C 2 -symmetric bisfluorenyl unit, 7,7′-diphenyl-7 H,7′ H -5,5′-bibenzo[ c ]fluorene-6,6′-diol (BIFOL), having central chirality was synthesized in an optically active form from (S)-(-)-BINOL-3,3′-dicarboxylic acid. The absolute configuration of the chiral bisfluorene derivative BIFOL was ascertained by single-crystal X-ray analysis. Furthermore, a new chiral phosphoric acid was synthesized from BIFOL and evaluated for enantioselective transfer hydrogenation.
- Someshwar, Nagamalla,Karthick, Muthupandi,Ramanathan, Chinnasamy Ramaraj
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supporting information
p. 2253 - 2261
(2017/10/06)
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