150760-92-2Relevant academic research and scientific papers
Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides
Hon, Yung-Son,Lu, Ling,Chang, Rong-Chi,Lin, Sheng-Wun,Sun, Pei-Pei,Lee, Chia-Fu
, p. 9269 - 9279 (2007/10/03)
Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.
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.
