1,3-Cyclobutanedione

1,3-Cyclobutandion Struktur.svg Cyclobutane-1,3-dione 78675-98-6 3-hydroxycyclobut-2-enone 15506-53-3 1,3-cyclobutanedione tautomer 25456 10004000 DTXSID30473940 27357 11829353 Q82303641 1S/C4H4O2/c5-3-1-4(6)2-3/h1-2H2 PZQGSZRQKQZCOJ-UHFFFAOYSA-N C1C(=O)CC1=O 1S/C4H4O2/c5-3-1-4(6)2-3/h1,5H,2H2 IHXWECHPYNPJRR-UHFFFAOYSA-N C1C(=CC1=O)O 4 4 2 colorless or white solid 1.12 g/cm3 119-120 1,3-Cyclobutanedione is an organic compound with the formula (CH2)2(CO)2. It is an isomer of 1,2-cyclobutanedione. The compound would be of little interest except that its tautomer is a subunit in some commercial dyes. In solution, 1,3-cyclobutanedione exists in equilibrium with a less stable tautomer, called squaraine, 3-hydroxycyclobut-2-enone.10.1021/jp9030915 Thermochemical Properties and Contribution Groups for Ketene Dimers and Related Structures from Theoretical Calculations 2009 Morales Giovanni Martínez Ramiro The Journal of Physical Chemistry A 113 30 8683–8703 19572711 2009JPCA..113.8683M Squaraine dyes are, formally at least, derivatives of squaraine. In such dyes, the ene-one tautomer predominates. thumb|left|280px|1,3-cyclobutanedione and its enol tautomer. The mixture of tautomers can be prepared by hydrolysis of 1-ethoxycyclobutene-3-one, which is prepared from the cycloaddition of ethoxyacetylene to ketene. 10.1021/ja00878a051 Cyclobutane-1,3-Dione 1962 Wasserman Harry H. Dehmlow Eckehard V. Journal of the American Chemical Society 84 19 3786–3787 1962JAChS..84.3786W Substituted derivatives A variety of substituted 1,3-Cyclobutanediones form upon spontaneous dimerization of disubstituted ketenes.10.1002/9780470771600.ch8 Synthetic uses of ketenes and allenes Ketenes, Allenes and Related Compounds: Vol. 1 (1980) 1980 Brady William T. 279–308 978-0-470-77160-0 PATAI'S Chemistry of Functional Groups Saul Patai 2,2,4,4-Tetramethylcyclobutanedione is thus formed by dehydrochlorination of isobutyryl chloride:R. Huisgen, P. Otto J. Am. Chem. Soc. The mechanism of dimerization of dimethylketene 90 19 5342–5343 1968 10.1021/ja01021a090 1968JAChS..90.5342H (CH3)2CHCOCl + Et3N -> (CH3)2C\dC\dO + Et3NHCl 2 (CH3)2C\dC\dO -> (CH3)2C)2(C\dO)2 Ketene itself dimerizes mainly to give the lactone called diketene as well as a small amount of 1,3-cyclobutanedione. Related compounds Moniliformin, a naturally occurring derivative of 3-hydroxycyclobut-2-enone References Category:Cyclobutanes Category:Cycloalkanones Category:Diketones