77415-39-5Relevant academic research and scientific papers
Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives
Iwasaki, Masayuki,Miki, Natsumi,Ikemoto, Yuichi,Ura, Yasuyuki,Nishihara, Yasushi
supporting information, p. 3848 - 3852 (2018/07/25)
An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.
Lithium- α-lithioacetate and β-lithiopropionate: Useful intermediates in organic synthesis
Pastor, Isidro M.,Yus, Miguel
, p. 5335 - 5339 (2007/10/03)
The reaction of chloroacetic acid and 3-chloropropionic acid with a base (LDA or Bu(n)Li, respectively) and then with an excess of lithium and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 5%) in the presence of different electrophiles [Bu'CHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe] in THF at -78°C leads, after hydrolysis with water, to the expected hydroxy acids, which in the second case are directly cyclised under acidic conditions to give the expected γ-lactones. (C) 2000 Elsevier Science Ltd.
ELECTRON-TRANSFER PROCESSES. NEW SYNTHESIS OF γ-LACTONES BY PEROXYDISULFATE OXIDATION OF ISOPROPYLBENZENES AND ALIPHATIC CARBOXYLIC ACIDS
Giordano, Claudio,Belli, Aldo,Citterio, Attilio,Minisci, Francesco
, p. 3559 - 3562 (2007/10/02)
A new synthesis of γ-lactones by peroxydisulfate oxidation of isopropylbenzenes is described.Evidence concerning the free-radical mechanism is reported; the intermediate formation of alkyl and benzyl radicals is evidenced by trapping them with quinoxaline.The role of the iron catalyst is discussed.
