Sonochemical Reactions of Lead Tetracarboxylates with Styrene

Ando, Takashi; Kimura, Takeshi; Lévêque, Jean–Marc; Lorimer, J.P.; Luche, Jean‐Louis; Mason, Timothy J.

doi:10.1021/jo981168u

Cited by 15 publications

(7 citation statements)

References 24 publications

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“…Moreover, the sonochemical reactivity of styrenes correlated well with their vapor pressures, while no correlation was found with the usual Hammett parameters that account for electronic effects. 72,73 In a further study, radical species formed in the sonochemical activation of styrenes were scavenged with pyrocatechol. A linear free-energy relationship could be established between rates of decomposition and vapor pressures of styrenes.…”

Section: Sonochemical Reactionsmentioning

confidence: 98%

Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications

2006

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Ultrasound, an efficient and virtually innocuous means of activation in synthetic chemistry, has been employed for decades with varied success. Not only can this high-energy input enhance mechanical effects in heterogeneous processes, but it is also known to induce new reactivities leading to the formation of unexpected chemical species. What makes sonochemistry unique is the remarkable phenomenon of cavitation, currently the subject of intense research which has already yielded thought-provoking results. This critical review is aimed at discussing the present status of cavitational chemistry and some of the underlying phenomena, and to highlight some recent applications and trends in organic sonochemistry, especially in combination with other sustainable technologies. (151 references.).

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Section: Sonochemical Reactionsmentioning

confidence: 98%

Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications

2006

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“…The notion that a sonochemical-based reaction is merely a mechanistic rather than a chemical operation was also discussed by Kegelaers et al [77] who, after repeating the same series of experiments as described by Ando et al [75], came to the different conclusion that sonochemical reaction served as a mechanistic approach akin to those from extensive stirring that shortens the reaction time [78] but by itself did not induce a chemical change. Despite various examples of 'true' [79][80][81] and 'false' [82,83] sonochemical reactions in literature, which so far remain as the most common explanations, it is necessary to acknowledge that the exact mechanism of sonication chemistry has not yet been clearly elucidated [84].…”

Section: Discussionmentioning

confidence: 99%

Sonochemical Reaction of Bifunctional Molecules on Silicon (111) Hydride Surface

2021

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While the sonochemical grafting of molecules on silicon hydride surface to form stable Si–C bond via hydrosilylation has been previously described, the susceptibility towards nucleophilic functional groups during the sonochemical reaction process remains unclear. In this work, a competitive study between a well-established thermal reaction and sonochemical reaction of nucleophilic molecules (cyclopropylamine and 3-Butyn-1-ol) was performed on p-type silicon hydride (111) surfaces. The nature of surface grafting from these reactions was examined through contact angle measurements, X-ray photoelectron spectroscopy (XPS) and atomic force microscopy (AFM). Cyclopropylamine, being a sensitive radical clock, did not experience any ring-opening events. This suggested that either the Si–H may not have undergone homolysis as reported previously under sonochemical reaction or that the interaction to the surface hydride via a lone-pair electron coordination bond was reversible during the process. On the other hand, silicon back-bond breakage and subsequent surface roughening were observed for 3-Butyn-1-ol at high-temperature grafting (≈150 °C). Interestingly, the sonochemical reaction did not produce appreciable topographical changes to surfaces at the nano scale and the further XPS analysis may suggest Si–C formation. This indicated that while a sonochemical reaction may be indifferent towards nucleophilic groups, the surface was more reactive towards unsaturated carbons. To the best of the author’s knowledge, this is the first attempt at elucidating the underlying reactivity mechanisms of nucleophilic groups and unsaturated carbon bonds during sonochemical reaction of silicon hydride surfaces.

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“…In the former case, the lead reagent adds to styrene to give a gem-diacetate via a carbocation, whereas the first stage of the radical pathway consists of the decomposition of lead tetraacetate to give the methyl radical, which then reacts with styrene. This was further investigated some years later by a team involving both Ando, Luche and Tim Mason [ 30 ].…”

Section: Explanations For Sonochemical Reactions Based On Electronmentioning

confidence: 99%

Jean-Louis Luche and the Interpretation of Sonochemical Reaction Mechanisms

Vînătoru

Mason

2021

Molecules

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Sonochemistry can be broadly defined as the science of chemical and physical transformations produced under the influence of sound. The use of sound energy is rather a young branch of chemistry and does not have the clear definitive rules of other, more established, divisions such as those in cycloaddition reactions or photochemistry. Nevertheless, there are a few guidelines which can help to predict what is going to happen when a reaction mixture is submitted to ultrasonic irradiation. Jean-Louis Luche, formulated some ideas of the mechanistic pathways involved in sonochemistry more than 30 years ago. He introduced the idea of “true” and “false” sonochemical reactions both of which are the result of acoustic cavitation. The difference was that the former involved a free radical component whereas only mechanical effects played a role the latter. The authors of this paper were scientific collaborators and friends of Jean-Louis Luche during those early years and had the chance to discuss and work with him on the mechanisms of sonochemistry. In this paper we will review the original rules (laws) as predicted by Jean-Louis Luche and how they have been further developed and extended in recent years.

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Sonochemical Reactions of Lead Tetracarboxylates with Styrene

Cited by 15 publications

References 24 publications

Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications

Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications

Sonochemical Reaction of Bifunctional Molecules on Silicon (111) Hydride Surface

Jean-Louis Luche and the Interpretation of Sonochemical Reaction Mechanisms

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