Pyridine Is an Organocatalyst for the Reductive Ozonolysis of Alkenes | Zendy

Rachel WillandCharnley | Zendy; Thomas J. Fisher | Zendy; Bradley M. Johnson | Zendy; Patrick H. Dussault | Zendy

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Pyridine Is an Organocatalyst for the Reductive Ozonolysis of Alkenes

Author(s) -

Rachel WillandCharnley,

Thomas J. Fisher,

Bradley M. Johnson,

Patrick H. Dussault

Publication year - 2012

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol300617r

Subject(s) - chemistry , ozonolysis , pyridine , nucleophile , oxidative cleavage , peroxide , fragmentation (computing) , ozone , organic chemistry , cleavage (geology) , photochemistry , catalysis , geotechnical engineering , fracture (geology) , computer science , engineering , operating system

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.

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