Synthesis and Photochemistry of 1-Iodocyclohexene:Influence of Ultrasound on Ionic vs. Radical Behaviour

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.

Sonochemical Preparation of Polymer Nanocomposites

“…Since the first report on the use of ultrasound to promoting reaction rates [ 1 ], the wide applications of sonochemistry in synthesis have attracted a lot of attention, in not only academia, but also in various fields of chemistry, materials science and chemical engineering [ 2 , 3 , 4 ]. Ultrasound is a kind of sound lying between 20 kHz and 10 MHz which cannot be heard by the human ear, and it has been reported that high-intensity ultrasound could exceed the attractive force of molecules to produce high concentrations of H· and OH· radicals in water [ 5 , 6 ].…”

Stereoelectronic effects: Perlin effects in cyclohexane‐derived compounds

“…This compound was prepared in analogy to a published protocol. [ 15 ] A solution of cyclohexanone 1 (500 mg, 3.24 mmol) in MeOH (2 ml) was added with stirring at °C to H 2 NNH 2 ·H 2 O (~85%, 1.7 ml, 1.67 g, 44.3 mmol) in a Pyrex tube. A colorless precipitate developed and the mixture was stirred for 1 h at 60°C and cooled to rt.…”

“…Oxime 4 [ 14 ] and an analogous hydrazone were synthesized with standard protocols starting with commercially available 4‐ tert ‐butylcyclohexanone ( 1 ). Reaction of 1 with hydrazine hydrate did not furnish the expected simple cyclohexylidenehydrazone but a 1,2‐dicyclohexylidenehydrazine 5 , [ 15 ] which we considered similarly suitable for the intended investigations (Scheme 1).…”

Ultrasound-Promoted Greener Synthesis of Novel Trifurcate 3-Substituted-chroman-2,4-dione Derivatives and Their Drug-Likeness Evaluation

“…In recent years, ultrasound-assisted organic synthesis (UAOS) utilizing environmentally benign reagents and conditions has been one of the most fascinating developments in the arena of modern synthetic chemistry owing to its green credentials [ 1 , 2 , 3 , 4 , 5 ]. The notable features of the aqueous UAOS come from its advantages such as easier manipulation, energy conservation, rate enhancement and insolubility of the final products which facilitates their isolation by simple filtration [ 6 , 7 ].…”