10341. Diketene
Nomenclature
CAS number: 674-82-8
4-Methylene-2-oxetanone; 3-buteno-β-lactone. C4H4O2; mol wt 84.07.
C 57.15%, H 4.80%, O 38.06%.
Description and references
Reactive acetoacetylation reagent; also used to introduce functionalized carbon units onto organic compds. Prepn from dimerization of ketene, q.v.: F. Chick, N. T. M. Wilsmore, J. Chem. Soc., Trans. 93, 946 (1908) DOI. Crystal structure and confirmation of molecular structure: L. Katz, W. N. Lipscomb, Acta Crystallogr. 5, 313 (1952) DOI. Process of cracking into ketene: S. Andreades, H. D. Carlson, Org. Synth. coll. vol. V, 679 (1973). Synthetic applications: S. I. Zavialov et al., Tetrahedron 22, 2003 (1966) DOI; A. Nudelman et al., Synthesis 1989, 387 DOI. Reviews: R. J. Clemens, Chem. Rev. 86, 241-318 (1986) DOI; N. Zohreh, Synlett 2008, 1913-1914 DOI.
