Pseudooxocarbons. Synthesis of 1,2,3-Tris(dicyanomethylene)croconate Salts. A New Bond-Delocalized Dianion, Croconate Blue

Journal of Organic Chemistry

Volumn 45, Issue 7, 1980, Pages 1338-1339

  Fatiadi, Alexander J ^a  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006689157     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01295a044     Document Type: Note

References (19)

1. A. J. Fatiadi, Abstracts, 178th National Meeting of the American Chemical Society, Washington, DC, Sept 9-14, 1979, No. ORGN 120.
2. A. J. Fatiadi, J. Am. Chem. Soc., 100, 2586 (1978).
3. A. J. Fatiadi, Synthesis, 165, 240 (1978).
4. R. West and J. Niu, “Nonbenzenoid Aromatics”, Vol. 1, J. P. Snyder, Ed., Academic Press, New York, 1969, Chapter 6; “The Chemistry of the Carbonyl Group”, Vol. 2, J. Zabicky, Ed., Interscience, New York, 1970, Chapter 4.
5. L. M. Schwartz, personal communication
6. All new compounds gave satisfactory elemental analyses.
7. Aqueous or alcoholic solutions of 3 (acid or salt) impart adherent stains to the skin; consequently, all operations require the use oi rubber or plastic gloves
8. The planarity of the dianion 3 still awaits confirmation by X-ray crystal structure analysis.
9. The broad peak was split into a poorly resolved sextet at 119.0, 119.6,119.3,118.7,117.9, and 117.7 ppm, apparently due to the staggered conformation of the cyano groups.
10. E. E. Sprenger and W. Ziegenbein, Angew. Chem., Int. Ed. Engl.; 7, 530 (1968).
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16. T. Fukunaga, J. Am. Chem. Soc., 98, 610 (1976); U.S. Patent 3963 769 (1976); Chem. Abstr., 86, 55052 (1977
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