16906-18-6Relevant academic research and scientific papers
About the Ozone Cleavage of Chloroprene and of 2-Chloro-3-methyl-1,3-butadiene in Methanol
Griesbaum, Karl,Meister, Martin
, p. 1573 - 1580 (2007/10/02)
Monoozonolyses of chloroprene (1a) and of 2-chloro-3-methyl-1,3-butadiene (1b) in methanol occur with more than 90percent at the non-chlorinated double bonds to afford the corresponding α,β-unsaturated oxo compounds 2 with selectivities of 96 and 80percent respectively.The latter subsequently react with methanol, and 2a also with the complementary fragment methoxymethyl hydroperoxide (5).The α,β-unsaturated methoxy hydroperoxides 3 which have also been obtained, are less stable than similarly structured, non-α-chlorinated methoxy hydroperoxides.Diozonolyses of 1a and 1b in methanol afforded in 50-60percent the corresponding α-oxocarboxylates (21) and/or the corresponding ketals.In addition, anomalous products were obtained viz. ca. 15percent of methyl hydroxyacetate (12d) from 1a and 1b, as well as ca. 30percent of dimethyl oxalate (27b) from 1a and ca. 35percent of methyl acetate (13) from 1b.The modes of formation of these products have been postulated according to model reactions.
