1151-15-1Relevant articles and documents
Direct Synthesis of γ-Substituted Phthalides Via ortho-Aryl Benzoic Acid Mediated Benzyl Radical Cyclization
Mahmoodi,Salehpour
, p. 875 - 878 (2003)
Direct synthesis of γ-substituted phthalids from related ortho-aryl benzoic acids with 48-85% yield are covered. The direct oxidation in the presence of peroxydisulphate-copper (II) chloride in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through very stable benzylic radical intermediate.
Direct synthesis of γ-substituted phthalides by cyclization of benzyl radicals generated from o-(arylmethyl)benzoic acids
Mahmoodi,Salehpour
, p. 1760 - 1763 (2003)
Direct oxidation of o-(arylmethyl)benzoic acids with sodium peroxysulfate-copper(II) chloride in water yields γ-substituted phthalides. The reaction is highly regioselective, and the corresponding γ-butyro-lactones are the only products formed through intermediate stable arylmethyl radicals.
Synthesis and conformational properties of 2,2′-dihydroxy-9,9′-bianthryl
Ghiaci,Bayat
, p. 609 - 612 (1996)
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Blicke,Weinkauff
, (1932)
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Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes
Wei, Hao-Zhao,Wei, Yin,Shi, Min
supporting information, p. 11201 - 11204 (2021/11/09)
An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for the rapid construction of isoquinolinone frameworks. This journal is
Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors
Felipe-Blanco, Diego,Gonzalez-Gomez, Jose C.
supporting information, p. 7735 - 7744 (2019/12/24)
The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.