23253-31-8Relevant academic research and scientific papers
Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation
Kawamura, Shin-Ichi,Takeuchi, Rika,Masuyama, Araki,Nojima, Masatomo,McCullough, Kevin J.
, p. 5617 - 5622 (2007/10/03)
Ozonolyses of 3-methyl- and 3-isopropyl-l-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtaine
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.
The stereochemistry of carbonyl oxides from ozonolysis of vinyl ethers
Bunnelle, William H.,Lee, Sang-Gi
, p. 8141 - 8144 (2007/10/02)
The geometries of the carbonyl oxides produced during ozonolysis of E- and Z-vinyl ethers have been assigned using the intramolecular trapping method. The alkoxy substituent exerts an anti-directive effect on formation of the carbonyl oxide; that is, the carbonyl oxide has a geometry opposite to that of the precursor vinyl ether.
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.
