Abstract
Heterocumulenes (B) are compounds with a substructure Het1=C=Het2, in which at least one of the groups “Het” is an O atom, an S atom, or an NR group (Figure 8.1). They can be regarded as anhydrides of the carbonic acid derivatives A. In fact, heterocumulenes are typically generated by eliminating water from such carbonic acid derivatives. Sometimes this occurs spontaneously, especially at elevated temperatures, but generally only upon treatment with a dehydrating reagent.
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References
8.1
W. E. Hanford, J. C Sauer, “Preparation of Ketenes and Ketene Dimers,” Org. React. 1946, 3, 108–140.
H. R. Seikaly, T. T. Tidwell, “Addition Reactions of Ketenes,” Tetrahedron 1986, 42, 2587.
H. Ulrich, “Chemistry and Technology of Isocyanates,” Wiley, Chichester, U. K., 1996.
M. V. Vovk, L. I. Samarsi, “N-Functionalized carbodiimides,” Russ. Chem. Rev 1992, 61, 297–305.
C. Agami, F. Couty, “The Reactivity of the N-Boc Protecting Group: An Underrated Feature,” Tetrahedron 2002, 58, 2701–2724.
8.2
D. Belli Dell’Amico, F. Calderazzo, L. Labella, F. Marchetti, G. Pampaloni, “Converting Carbon Dioxide into Carbamato Derivatives,” Chem. Rev. 2003, 103, 3857–3897.
S. Z. Zard, “On the Trail of Xanthates: Some New Chemistry from an Old Functional Group,” Angew. Chem. Int. Ed. Engl. 1997, 36, 672–685.
A.-A. G. Shaikh, S. Sivaram, “Organic Carbonates,” Chem. Rev. 1996, 96, 951–976.
J. P. Parrish, R. N. Salvatore, K. W. Jung, “Perspectives on Alkyl Carbonates in Organic Synthesis,” Tetrahedron 2000, 56, 8207–8237.
E. Däbritz, “Syntheses and Reactions of O,N,N′-Trisubstituted Isoureas,” Angew. Chem. Int. Ed. Engl. 1966, 5, 470–477.
V. F. Pozdnev, “Activation of Carboxylic Acids by Pyrocarbonates. Scope and Limitations,” Org. Prep. Proced. Int. 1998, 30, 631–655.
Further Reading
Y. Ono, “Dimethyl Carbonate for Environmentally Benign Reactions,” Pure Appl. Chem. 1996, 68, 367–376.
P. Tundo, M. Selva, “The Chemistry of Dimethyl Carbonate,” Acc. Chem. Res. 2002, 35, 706–716.
L. Cotarca, P. Delogu, A. Nardelli, V. Sunjic, “Bis(trichloromethyl) Carbonate in Organic Synthesis,” Synthesis 1996, 553–576.
Y. I. Matveev, V. I. Gorbatenko, L. I. Samarai, “1,1-Dihaloalkyl Heterocumulenes: Synthesis and Reactions,” Tetrahedron 1991, 47, 1563–1601.
N. A. Nedolya, B. A. Trofimov, A. Senning, “α,β-Unsaturated Isothiocyanates,” Sulfur Rep. 1996, 17, 183–395.
J. H. Rigby, “Vinyl Isocyanates as Useful Building Blocks for Alkaloid Synthesis,” Synlett 2000, 1–12.
W. D. Rudorf, “Reactions of Carbon Disulfide with C-Nucleophiles,” Sulfur Rep. 1991, 11, 51–141.
G. Maier, H. P. Reisenauer, R. Ruppel, “Matrix Isolation of Chalcogeno Heterocumulenes,” Sulfur Rep. 1999, 21, 335–355.
A. A. Bakibayev, V. V. Shtrykova, “Isoureas: Synthesis, Properties, and Applications,” Russ. Chem. Rev. 1995, 64, 929–938.
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(2010). Carbonic Acid Derivatives and Heterocumulenes and Their Interconversion. In: Harmata, M. (eds) Organic Mechanisms. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-03651-4_8
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