Department of Chemistry, University of Nebraska-Lincoln , Lincoln, Nebraska 68588-0304, United States.
Org Lett. 2012 May 4;14(9):2242-5. doi: 10.1021/ol300617r. Epub 2012 Apr 18.
Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.
尽管烯烃的臭氧裂解通常会产生过氧化物中间体，这些中间体必须在后续步骤中分解，但在吡啶存在下的臭氧化直接通过既不消耗吡啶也不生成任何可检测到的过氧化物的过程生成酮或醛。该反应被假设涉及通过形成两性离子过氧缩醛来促进羰基氧化物的亲核断裂。
