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1 2007

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Facile One-Pot Synthesis of 2-(3,4-Dihydroxyphenyl)-2-phenyl-2H-indene in the Presence of 2-Phenyl-1,3-indandione

Shamsipur M., Hosseiny Davarani S., Bayandori-Moghaddam A., Nematollahi D., Fakhari A.

Polish Journal of Chemistry

2007

Vol. 81, nr 2

237-247

The electrooxidation of 3-substituted catechols (1a–1c) has been studied in the presence of 2-phenyl-1,3-indandione (3) in water + acetonitrile (90/10 v/v) solution, using the electrochemical and spectroelectrochemical methods. The o-benzoquinones (2a–2c) derived from catechols (1a–1c) precipitate out according toMichael addition reactionswith 2-phenyl-1,3-indandione (3) to form the corresponding 2-(3,4-dihydroxyphenyl)-2- phenyl-2H-indene derivatives (5a–5c). An EC mechanism was proposed for the electrode process. The efficient electrochemical syntheses of the new catechol derivatives (5a-5c) were performed at a carbon rod electrode in an undivided cell at high yields.