ChemInform Abstract: SEMIEMPIRICAL CALCULATIONS OF INTERNAL BARRIERS TO ROTATION AND RING PUCKERING. II. A MINDO 3 STUDY

Combs, Leon L.; Rossie, Michael

doi:10.1002/chin.197624051

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Small, oxygen-containing ring structures are commonly used in synthetic and pharmaceutical chemistry − and may also occur as intermediates during the oxidation of hydrocarbon radicals. − Cyclic structures exhibiting a high degree of ring strain are often prone to thermal decomposition, even at relatively low temperatures, due to their instability. − The cyclic ketone 3-oxetanone (Figure ) is an archetype of such small, ring-strained compounds. Most studies of 3-oxetanone have focused on how ring strain and the electronic interactions of atoms in the ring relate to its planar equilibrium geometry. ,− The occurrence of 3-oxetanone is suspected in the decomposition of the acetonylperoxy radical, an intermediate formed during the atmospheric processing of acetone . Atmospheric degradation of acetone produces the acetonyl radical, CH 3 C(O)CH 2 , which reacts with O 2 to form the acetonylperoxy radical.…”

Section: Introductionmentioning

confidence: 99%

Pyrolysis Reactions of 3-Oxetanone

et al. 2015

View full text Add to dashboard Cite

The pyrolysis products of gas-phase 3-oxetanone were identified via matrix-isolation Fourier transform infrared spectroscopy and photoionization mass spectrometry. Pyrolysis was conducted in a hyperthermal nozzle at temperatures from 100 to 1200 °C with the dissociation onset observed at ∼600 °C. The ring strain in the cyclic structure of 3-oxetanone causes the molecule to decompose at relatively low temperatures. Previously, only one dissociation channel, producing formaldehyde and ketene, was considered as significant in photolysis. This study presents the first experimental measurements of the thermal decomposition of 3-oxetanone demonstrating an additional dissociation channel that forms ethylene oxide and carbon monoxide. Major products include formaldehyde, ketene, carbon monoxide, ethylene oxide, ethylene, and methyl radical. The first four products stem from initial decomposition of 3-oxetanone, while the additional products, ethylene and methyl radical, are believed to be due to further reactions involving ethylene oxide.

show abstract