Detection of a Criegee Intermediate with an Unsaturated Hydrocarbon Substituent: Fourier-Transform Microwave Spectroscopy of Methyl Vinyl Ketone Oxide

2020 ◽  
Vol 124 (30) ◽  
pp. 6203-6206
Author(s):  
Yasuki Endo ◽  
Henryk A. Witek ◽  
Chen-An Chung ◽  
Yuan-Pern Lee
Keyword(s):  
Fourier Transform ◽  
Unsaturated Hydrocarbon ◽  
Microwave Spectroscopy ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Methyl Vinyl ◽  
Fourier Transform Microwave Spectroscopy

scholarly journals Infrared characterization of formation and resonance stabilization of the Criegee intermediate methyl vinyl ketone oxide

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Chen-An Chung ◽  
Yuan-Pern Lee
Keyword(s):  
High Pressure ◽  
Fourier Transform ◽  
Reaction Mechanism ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Fourier Transform Spectrometer ◽  
Methyl Vinyl ◽  
Criegee Intermediates ◽  
Resonance Stabilization

AbstractMethyl vinyl ketone oxide (MVKO) is an important Criegee intermediate in the ozonolysis of isoprene. MVKO is resonance stabilized by its allyl moiety, but no spectral characterization of this stabilization was reported to date. In this study, we photolyzed a mixture of 1,3-diiodo-but-2-ene and O2 to produce MVKO and characterized the syn-trans-MVKO, and tentatively syn-cis-MVKO, with transient infrared spectra recorded using a step-scan Fourier-transform spectrometer. The O‒O stretching band at 948 cm−1 of syn-trans-MVKO is much greater than the corresponding bands of syn-CH3CHOO and (CH3)2COO Criegee intermediates at 871 and 887 cm−1, respectively, confirming a stronger O‒O bond due to resonance stabilization. We observed also iodoalkenyl radical C2H3C(CH3)I upon photolysis of the precursor to confirm the fission of the terminal allylic C‒I bond rather than the central vinylic C‒I bond of the precursor upon photolysis. At high pressure, the adduct C2H3C(CH3)IOO was also observed. The reaction mechanism is characterized.

Copolymerization of methyl vinyl ketone with styrene in the presence of cobalt(II) nitrate

1991 ◽  
Vol 47 (1) ◽  
pp. 329-336 ◽  
Author(s):  
Seizo Masuda ◽  
Keiji Minagawa ◽  
Masami Tanaka ◽  
Yutaka Asahi
Keyword(s):  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Methyl Vinyl
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