Cyclobutanone carbon dioxide

The trapping of lithiohalocyclopropanes by carbon dioxide, aldehydes and acid chlorides, respectively, constitutes a useful route to the corresponding cyclopropanecarboxylic acids, alcohols and ketones. In the case of ketones an intramolecular loss of lithium bromide may take place yielding spiroepoxides which in turn may be isomerized to cyclobutanones. 

Hara et al., 2005). THP, cyclobutanone, and cyclohexane also showed pressure reductions for carbon dioxide hydrate formation (Mooijer-van den Heuvel et al., 2001). THP, cyclobutanone, cyclohexane, and methylcyclohexane all reduced not only the pressure for propane hydrate formation, but also shifted the H-Lw-Lc3H8 line to lower temperature (Mooijer-van den Heuvel et al., 2002). 

Cyclobutanone is an important synthetic starting material (e.g. see Expt 5.41) recently a simple synthesis from readily available materials has been reported.6 The synthesis (Expt 7.13) involves the formation of l,3-bis[bromo-magnesio]propane and its further reaction with carbon dioxide to form the complex (36), which precipitates from solution thus simplifying the purification procedure. Although the overall yield is low (13%), this is compensated for by the cheapness of the reagents and the simplicity of the procedure. 

Diorganomagnesium compounds have, apart from simple derivatixation reactions with ketones or carbon dioxide, not often been used in organic. synthesis. An exception is 60a which (in the crude reaction mixture) on slow exposure to gaseous carbon dioxide (3 h al room temperature) gave 33% of cyclobutanone (70) this constitutes the most efficient preparation of this compound (441 (Scheme 1 1.24). 

Mooijer-van den Heuvel MM, Witteman R, Peters CJ (2001) Phase behaviour of gas hydrates of carbon dioxide in the presence of tetrahydropyran, cyclobutanone, cyclohexane and methylcyclohexane. Fluid Phase Equilib 182(l-2) 97-110... 

Craz Duarte, A. R. Mooijer-van den Heuvel, M. M. Duarte, C. M. M. Peters, C. J. Measurement ad modelling of bubble and dew points in the binary systems carbon dioxide + cyclobutanone and propane + cyclobutanone. Fluid Phase Equilib. 2003, 214, 121-136. 

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