79698-42-3Relevant academic research and scientific papers
Ozonolysis of Vinyl Ethers in Solution and on Polyethylene
Griesbaum, Karl,Kim, Woo-Sun,Nakamura, Norinaga,Mori, Mitsuyuki,Nojima, Masatomo,Shigekazu, Kusabayashi
, p. 6153 - 6161 (2007/10/02)
Ozonolyses of the vinyl ethers 1a-f in methanol afforded almost exclusively the corresponding α-methoxy hydroperoxides 4, suggesting the preferred formation of the carbonyl oxides 2.In aprotic solvents including methyl formate, the predominant modes of decay of the carbonyl oxides 2 were cyclodimerization, reduction, and rearrangement, yet no ozonide formation.By contrast, ozonolyses of 1a-f on polyethylene gave the α-methoxy-substituted ozonides 14 in fair yields.Ozonolyzes of 1a-f in the presence of added carbonyl compounds 6 in methylene chloride or ether yielded the corresponding cross ozonides.Judged from the ozonide yields, the reactivities of the carbonyl compounds follow the sequence: (ClCH2)2C=O > ClCH2COCH3 > (CH3)2C=O and 2-CF3C6H4CHO > PhCHO.
Oxygenation of Aromatic Vinyl Ethers. A Noticeable Formation of Epoxides and Reaction Mechanism
Kanno, Tatsuya,Hisaoka, Motoyuki,Sakuragi, Hirochika,Tokumaru, Katsumi
, p. 2330 - 2336 (2007/10/02)
cis-β-Alkoxystyrenes such as cis-β-methoxy-, cis-β-ethoxy-, and cis-β-isopropoxystyrene were autoxidized as neat at room temperature in the dark even in the absence of any radical generator.UV-irradiation and the use of a radical generator facilitated the oxygenation of these olefins.These oxidations afforded the corresponding epoxides or their derivatives in considerable yields as well as carbonyl compounds resulting from oxidative cleavage of the double bonds.The mechanisms for these oxidations are proposed to involve free-radical chain pathways and charge-transfer complexes between the olefins and oxygen play an important role in the initiation steps.
