Synthesis of new 2,3-perfluoroalkyl- and perfluoroaryl-1,4-diazabutadienes (α-diimines)

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8523-8527

  Diel, Bruce N ^a   Deardorff, Peter J ^a   Zelenski, Catherine M ^a  

^a MIDWEST RESEARCH INSTITUTE   (United States)

Author keywords

Diimines; Diones; Halogen compounds; Halogens; N imides

Indexed keywords

FLUORESCENT DYE; FLUOROBENZENE; IMINE; ORGANOCHLORINE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; ORGANOLITHIUM COMPOUND;

ARTICLE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033521084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01692-5     Document Type: Article

References (17)

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6. Phenanthrenequinone-(9,10)-bis(trimethylsilyl)diimine and N,N′-bis(trimethylsilyl)-1,2-diphenylethanediimine.
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10. 3,100].
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12. A complete summary of all spectral data is included in the supplementary materials.
13. The structure determination was carried out by Professor A. Rheingold and co-workers at the University of Delaware, for which we are grateful. Crystal data collection and refinement parameters are given in the supplementary materials. A suitable crystal for data collection was selected and mounted in a nitrogen-flushed, thin-walled capillary. Data was collected with a Siemens P4 diffractometer equipped with a SMART/CCD detector. The systematic absences in the diffraction data are consistent with the space groups Cc and C2/c. E-statistic suggested the centrosymmetric space group option, C2/c, which yielded chemically reasonable and computationally stable results of refinement. The structure was solved using direct methods, completed by subsequent difference Fourier synthesis and refined by full-matrix least-squares procedures. All non-hydrogen atoms were refined with anisotropic displacement coefficients. All hydrogen atoms were treated as idealized contributions. All software and sources of the scattering factors are contained in the SHELXTL (version .03) program library (G. Sheldrick, Siemens XRD, Madison, WI). Program DIFABS is described in: Walker, N.; Stuart, D. Acta Cryst. 1983, A39, 158.
14. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd Edition; Wiley-Interscience: New York, 1985; pp. 18-21, and references cited therein.
15. Semiempirical molecular orbital calculations (PM3 static energy and geometry optimization) were accomplished using Alchemy 2000, from Tripos, Inc., St. Louis, MO.
16. Diel, B. N.; Deardorff, P. J.; Zelenski, C. M. Inorg. Chem., submitted for publication.
17. Diel, B. N.; Deardorff, P. J.; Taylor, G. R.; Grisham, C. G.; Zelenski, C. M. Organometallics, submitted for publication.