Gas-phase detection of oxirene

Area of Science:

• Organic Chemistry
• Physical Chemistry
• Astrochemistry

Background:

• Oxirenes are highly strained 4π Hückel antiaromatic organic molecules.
• They are key reactive intermediates in the Wolff rearrangement and found in interstellar environments.
• The isolation of oxirene (c-C2H2O) has been elusive due to short lifetimes and ring-opening tendencies.

Purpose of the Study:

• To prepare and detect the elusive oxirene (c-C2H2O) molecule.
• To investigate novel strategies for synthesizing highly strained organic transients.
• To advance the fundamental understanding of chemical bonding and stability in strained cyclic molecules.

Main Methods:

• Preparation of oxirene in low-temperature methanol-acetaldehyde matrices via ketene isomerization.
• Energetic processing involving resonant energy transfer to matrix molecules.
• Detection of gas-phase oxirene using soft photoionization and reflectron time-of-flight mass spectrometry.

Main Results:

• Successful preparation and isolation of oxirene (c-C2H2O) in a low-temperature matrix.
• Detection of oxirene in the gas phase after sublimation from the matrix.
• Demonstration of a versatile strategy for synthesizing highly strained transients.

Conclusions:

• The study reports the first preparation and detection of oxirene (c-C2H2O).
• Findings provide insights into the stability and bonding of strained cyclic organic molecules.
• The developed method offers a versatile approach for synthesizing reactive intermediates in extreme environments.