23246-12-0Relevant articles and documents
Highly efficient biphasic ozonolysis of alkenes using a high-throughput film-shear flow reactor
Kendall, Alexander J.,Barry, Justin T.,Seidenkranz, Daniel T.,Ryerson, Ajay,Hiatt, Colin,Salazar, Chase A.,Bryant, Dillon J.,Tyler, David R.
supporting information, p. 1342 - 1345 (2018/03/27)
A new method for ozonolysis of alkenes using a continuous flow film-shear reactor was developed. The reactor uses a shearing microfluidic mixing chamber to provide biphasic mixing of an organic phase and aqueous phase with ozone gas. The H2O acts as an in situ reducing agent for the carbonyl oxide intermediate, providing ketones and aldehydes directly from the reaction mixture. Flow rates of up to 1.0 mmol/min (alkene) with an ozone reaction efficiency of >70% were achieved. Aryl conjugated olefins reacted to form carbonyl species in good yields on a multi-gram scale; however, alkyl olefins reacted with ozone to predominantly form secondary ozonides. The discrepancy in product distributions between alkyl and aryl olefins likely originates from the electronic stability of the carbonyl oxide intermediate, which is longer lived for aryl derivatives due to conjugation.
Electronic Effects in the Reaction of Carbonyl Oxides with Aldehydes
Murray, Robert W.,Morgan, Michael M.
, p. 684 - 687 (2007/10/02)
Electronic effects in the third step of the Criegee mechanism of ozonolysis, i.e., the reaction of a carbonyl oxide with a carbonyl compound, were studied by using a non-ozone source of carbonyl oxides as well as by an ozonolysis method.Benzophenone oxide
