150760-93-3Relevant academic research and scientific papers
'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.
The mechanistic study and synthetic applications of the base treatment in the ozonolytic reactions
Hon, Yung-Son,Lin, Sheng-Wun,Lu, Ling,Chen, Yao-Jung
, p. 5019 - 5034 (2007/10/02)
The E1cb mechanism is the overwhelming process in the reaction of bases and ozonides. As a quenching agent in the ozonolysis of a variety of alkenes, the reactions involving triethylamine often gave better yields and proceeded faster than those involving methyl sulfide. On the other hand, in the presence of 4 A molecular sieves, the secondary amines reacted with mono- and 1,1-di-substituted ozonides to afford the reductive amination products in high yields. The formation of ammonium formate in the reaction mixture also supported the E1cb mechanism in the reaction of ozonide and amine.
A convenient and efficient workup of ozonolysis reactions using triethylamine
Hon,Lin,Chen
, p. 1543 - 1553 (2007/10/02)
Comparisons were made between triethylamine and methyl sulfide for their use as a quenching agent in the ozonolysis of a variety of alkenes. The reactions involving triethylamine often gave better yields and proceeded faster than those of involving methyl sulfide. The role of triethylamine played as base instead of reducing agent in the reaction.
