20525-41-1Relevant academic research and scientific papers
Fragmentation of carbonyl oxides by N-oxides: An improved approach to alkene ozonolysis
Schwartz, Chris,Raible, Joseph,Mott, Kyle,Dussault, Patrick H.
, p. 3199 - 3201 (2007/10/03)
Ozonolysis of alkenes in the presence of amine N-oxides results in the direct formation of aldehydes. This reaction, which appears to involve an unprecedented trapping and fragmentation of the short-lived carbonyl oxide intermediates, avoids the hazards associated with generation and isolation of ozonides or other peroxide products.
'Reductive ozonolysis' via a new fragmentation of carbonyl oxides
Schwartz, Chris,Raible, Joseph,Mott, Kyle,Dussault, Patrick H.
, p. 10747 - 10752 (2007/10/03)
This account describes the development of methodologies for 'reductive' ozonolysis, the direct ozonolytic conversion of alkenes into carbonyl groups without the intermediacy of 1,2,4-trioxolanes (ozonides). Ozonolysis of alkenes in the presence of DMSO produces a mixture of aldehyde and ozonide. The combination of DMSO and Et3N results in improved yields of carbonyls but still leaves unacceptable levels of residual ozonides; similar results are obtained using secondary or tertiary amines in the absence of DMSO. The influence of amines is believed to result from conversion to the corresponding N-oxides; ozonolysis in the presence of amine N-oxides efficiently suppresses ozonide formation, generating high yields of aldehydes. The reactions with amine oxides are hypothesized to involve an unprecedented trapping of carbonyl oxides to generate a zwitterionic adduct, which fragments to produce the desired carbonyl group, an amine, and 1O2.
