Synthesis and Low Temperature Spectroscopic Observation of 1,3,5-Trioxane-2,4,6-Trione: The Cyclic Trimer of Carbon Dioxide | Zendy

Michael J. Rodig | Zendy; Arthur W. Snow | Zendy; Paul Scholl | Zendy; Simon Rea | Zendy

Open Access

Synthesis and Low Temperature Spectroscopic Observation of 1,3,5-Trioxane-2,4,6-Trione: The Cyclic Trimer of Carbon Dioxide

Author(s) -

Michael J. Rodig,

Arthur W. Snow,

Paul Scholl,

Simon Rea

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b00647

Subject(s) - chemistry , trimer , trioxane , isobutyraldehyde , carbon 13 nmr , aldehyde , organic chemistry , dimer , catalysis , polymerization , polymer

1,3,5-Trioxane-2,4,6-trione (cyclic trimer of CO2) is the product of a four-step synthesis: chlorination of isobutyraldehyde; cyclotrimerization of 2-chloro-2-methylpropanal; dehydochlorination of 2,4,6-tris(2-chloropropan)-2-yl-1,3,5-trioxane; ozonolysis at -80 °C of 2,4,6-tri(propan-2-ylidene)-1,3,5-trioxane. This trioxane-trione is detected in solution at temperatures between -80 to -40 °C, and its conversion to CO2 is monitored by (13)C NMR and FTIR. The CO2 trimer has a half-life of approximately 40 min at -40 °C.

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