Synthesis and fragmentation of 2,2-diazido-1,3,2-dioxasila-5-cycloheptenes. The chemical vapor deposition of SiO2

Journal of the American Chemical Society

Volumn 118, Issue 50, 1996, Pages 12752-12757

  Herges, Rainer ^a   Starck, Felix ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

SILICON DIOXIDE;

ARTICLE; DRUG MANUFACTURE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030475725     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9615886     Document Type: Article

References (42)

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18. The connectivity was checked by intrinsic reaction coordinate analysis see: (a) Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 93, 1840-1851. (b) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. (c) Fukui, K. Pure Appl. Chem. 1982, 54, 1825-1836.
19. The connectivity was checked by intrinsic reaction coordinate analysis see: (a) Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 93, 1840-1851. (b) Fukui, K. Acc. Chem. Res. 1981, 14, 363-368. (c) Fukui, K. Pure Appl. Chem. 1982, 54, 1825-1836.
20. DFT methods intrinsically include correlation energy. This was first recognized by Slater: Slater, J. C. Phys. Rev. 1951, 81, 385. For a quantitative assessment we calculated the singlet potential energy surface for the homolytic dissociation of ethane in two methyl radicals at the B3LYP/6-31G* and the UB3LYP/6-31G* level. The energies are identical within the numerical error of the Gaussian94 program up to a C-C distance of 2.4 Å. At this point according to a CAS(10,8)/6-31G* calculation (10-electron 8-orbital complete active space) 20% of higher configurations contribute to the overall wavefunction: Herges, R. Unpublished results.
21. DFT methods intrinsically include correlation energy. This was first recognized by Slater: Slater, J. C. Phys. Rev. 1951, 81, 385. For a quantitative assessment we calculated the singlet potential energy surface for the homolytic dissociation of ethane in two methyl radicals at the B3LYP/6-31G* and the UB3LYP/6-31G* level. The energies are identical within the numerical error of the Gaussian94 program up to a C-C distance of 2.4 Å. At this point according to a CAS(10,8)/6-31G* calculation (10-electron 8-orbital complete active space) 20% of higher configurations contribute to the overall wavefunction: Herges, R. Unpublished results.
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23. -1. (a) Tardy, D. C.; Ireton, R.; Gordon, A. S. J. Am. Chem. Soc. 1979, 101, 1508-1514. The fragmentation proceeds under flash pyrolysis conditions at 700-800°C, ∼10 Torr, time of contact 0.01-0.03 s with ∼90% yield. (b) Rice, F. O.; Ruoff, P. M.; Rodowskas, E. L. J. Am. Chem. Soc. 1938, 60, 955-961.
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34. See also: (a) Wiberg, E.; Michaud, H. Z. Naturforsch. 1954, 9b, 500. (b) Nachr. Chem. Techn. 1970, 18, 26-27.
35. For similar cyclizations of methyl- and phenyl-substituted dichlorosilanes with diols, see: (a) Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689-2692. (b) Calas, R.; Nicou, P. C. R. Acad. Sci. Paris 1959, 249, 1011-1013. (c) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1984, 270, 25-37. (d) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1985, 291, 153-157.
36. For similar cyclizations of methyl- and phenyl-substituted dichlorosilanes with diols, see: (a) Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689-2692. (b) Calas, R.; Nicou, P. C. R. Acad. Sci. Paris 1959, 249, 1011-1013. (c) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1984, 270, 25-37. (d) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1985, 291, 153-157.
37. For similar cyclizations of methyl- and phenyl-substituted dichlorosilanes with diols, see: (a) Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689-2692. (b) Calas, R.; Nicou, P. C. R. Acad. Sci. Paris 1959, 249, 1011-1013. (c) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1984, 270, 25-37. (d) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1985, 291, 153-157.
38. For similar cyclizations of methyl- and phenyl-substituted dichlorosilanes with diols, see: (a) Krieble, R. H.; Burkhard, C. A. J. Am. Chem. Soc. 1947, 69, 2689-2692. (b) Calas, R.; Nicou, P. C. R. Acad. Sci. Paris 1959, 249, 1011-1013. (c) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1984, 270, 25-37. (d) Cragg, R. H.; Lane, R. D. J. Organomet. Chem. 1985, 291, 153-157.
39. A similar kinetic stabilization toward dimerization and polymerization was observed by the reaction of dichlorodimethylsilane with ethylene glycol which gives only dimers and polymers (ref 20a) and pinacol which yields the monomeric 1,3,2-dioxasilacyclopentane (ref 20c).
40. Ullmanns Encyklopädie der technischen Chemie, 4.Aufl., Bd.21; Verlag Chemie: Weinheim, Germany, 1979; S.481ff
41. For a review see: (a) Bradley, D. C. Chem. Rev. 1989, 89, 1317-1322. For a recent publication, see: (b) Narula, C. K.; Varshney, A.; Riaz, U. Chem. Vap. Deposition 1996, 2, 13-15.
42. For a review see: (a) Bradley, D. C. Chem. Rev. 1989, 89, 1317-1322. For a recent publication, see: (b) Narula, C. K.; Varshney, A.; Riaz, U. Chem. Vap. Deposition 1996, 2, 13-15.