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Carbonic Acid Derivatives and Heterocumulenes and Their Interconversion

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Organic Mechanisms

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.

Survey of the interconversion of carbonic acid derivatives and heterocumulenes.

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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.

    Google Scholar 

  • H. R. Seikaly, T. T. Tidwell, “Addition Reactions of Ketenes,” Tetrahedron 1986, 42, 2587.

    Article  CAS  Google Scholar 

  • H. Ulrich, “Chemistry and Technology of Isocyanates,” Wiley, Chichester, U. K., 1996.

    Google Scholar 

  • M. V. Vovk, L. I. Samarsi, “N-Functionalized carbodiimides,” Russ. Chem. Rev 1992, 61, 297–305.

    Article  Google Scholar 

  • C. Agami, F. Couty, “The Reactivity of the N-Boc Protecting Group: An Underrated Feature,” Tetrahedron 2002, 58, 2701–2724.

    Article  CAS  Google Scholar 

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.

    Article  Google Scholar 

  • 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.

    Article  Google Scholar 

  • A.-A. G. Shaikh, S. Sivaram, “Organic Carbonates,” Chem. Rev. 1996, 96, 951–976.

    Article  CAS  Google Scholar 

  • J. P. Parrish, R. N. Salvatore, K. W. Jung, “Perspectives on Alkyl Carbonates in Organic Synthesis,” Tetrahedron 2000, 56, 8207–8237.

    Article  CAS  Google Scholar 

  • E. Däbritz, “Syntheses and Reactions of O,N,N′-Trisubstituted Isoureas,” Angew. Chem. Int. Ed. Engl. 1966, 5, 470–477.

    Article  Google Scholar 

  • V. F. Pozdnev, “Activation of Carboxylic Acids by Pyrocarbonates. Scope and Limitations,” Org. Prep. Proced. Int. 1998, 30, 631–655.

    Article  CAS  Google Scholar 

Further Reading

  • Y. Ono, “Dimethyl Carbonate for Environmentally Benign Reactions,” Pure Appl. Chem. 1996, 68, 367–376.

    Article  CAS  Google Scholar 

  • P. Tundo, M. Selva, “The Chemistry of Dimethyl Carbonate,” Acc. Chem. Res. 2002, 35, 706–716.

    Article  CAS  Google Scholar 

  • L. Cotarca, P. Delogu, A. Nardelli, V. Sunjic, “Bis(trichloromethyl) Carbonate in Organic Synthesis,” Synthesis 1996, 553–576.

    Google Scholar 

  • Y. I. Matveev, V. I. Gorbatenko, L. I. Samarai, “1,1-Dihaloalkyl Heterocumulenes: Synthesis and Reactions,” Tetrahedron 1991, 47, 1563–1601.

    Article  CAS  Google Scholar 

  • N. A. Nedolya, B. A. Trofimov, A. Senning, “α,β-Unsaturated Isothiocyanates,” Sulfur Rep. 1996, 17, 183–395.

    Article  CAS  Google Scholar 

  • J. H. Rigby, “Vinyl Isocyanates as Useful Building Blocks for Alkaloid Synthesis,” Synlett 2000, 1–12.

    Google Scholar 

  • W. D. Rudorf, “Reactions of Carbon Disulfide with C-Nucleophiles,” Sulfur Rep. 1991, 11, 51–141.

    Article  CAS  Google Scholar 

  • G. Maier, H. P. Reisenauer, R. Ruppel, “Matrix Isolation of Chalcogeno Heterocumulenes,” Sulfur Rep. 1999, 21, 335–355.

    Article  CAS  Google Scholar 

  • A. A. Bakibayev, V. V. Shtrykova, “Isoureas: Synthesis, Properties, and Applications,” Russ. Chem. Rev. 1995, 64, 929–938.

    Article  Google Scholar 

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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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