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Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina CH-2, SK-842 15, Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 14 December 2006; in revised form: 24 January 2007 / Accepted: 25 January 2007 / Published: 16 February 2007
Abstract: Simultaneous application of UV light and ultrasonic irradiation to a reaction mixture containing 1-iodocyclohexene is reported. The irradiation of 1-iodocyclohexene in methanol was carried out with or without addition of zinc. The effect of ultrasound or mechanical stirring on this solid-liquid system was also compared. The irradiation of 1-iodocyclohexene in methanol in the presence of zinc increases the yield of the nucleophilic trapping product, compared with the yield after irradiation in the absence of zinc. The photodegradation of 1-iodocyclohexene was slightly accelerated after addition of zinc. A rapid formation of radical product was accompanied by substantial decrease of 1-iodocyclohexene after application of ultrasound and irradiation without the zinc. The ultrasound significantly affects the photobehaviour of this reaction, predominantly its radical route. The joint application of ultrasound and zinc contributes positively to the production of radical and ionic products. The sonochemical stirring is more effective than mechanical stirring.
Keywords: Ultrasound; photochemistry; 1-iodocyclohexene
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Blaskovicova, M.; Gaplovsky, A.; Blasko, J. Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour. Molecules 2007, 12, 188-193.
Blaskovicova M, Gaplovsky A, Blasko J. Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour. Molecules. 2007; 12(2):188-193.
Blaskovicova, Marika; Gaplovsky, Anton; Blasko, Jaroslav. 2007. "Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour." Molecules 12, no. 2: 188-193.