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Scriven, E. F. V., Ed.; Academic Press: New York, Chapter 8
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(c) Wentrup, C. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984; Chapter 8, p 395 f.
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0001343262
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The thermal ring contractions of 9-phenanthridylnitrene to a mixture of 9- and 4-cyanocarbazoles, its ring expansion to dibenzo-[d,f]-1,3- diazcycloheptatetraene, and the dimerization of the latter to a stable 2,4-diimino-1,2-diazetidine derivative have been reported: (a) Wentrup, C.; Thetaz, C.; Mayor, C. Helv. Chim. Acta 1972, 55, 2633.
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Mongnchi, K.; Itoh, T.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 2004, 126, 11900.
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Smolinsky, G.; Snyder, L. C.; Wasserman, E. Rev. Mod. Phys. 1963, 35, 576.
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(a) Bednarek, P.; Kvaskoff, D.; Wentrup, C. The University of Queensland, Brisbane, Australia. Unpublished results, 2004-2005.
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25444451499
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note
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(c) Selected examples of (D,p) values for several nitrenes: 2-pyrimidyl (1.217, 1.703), 4-pyridyl (1.107, 1.6312), 3-pyridazinyl (1.066, 1.6374), 2-pyridyl (1.051, 1.6393), phenyl (0.998, 1.5993), 2-naphthyl (0.925, 1.5605), 9-phenanthryl 9T (0.811, 1.4567), 1-naphthyl (0.793, 1.4891), 1-anthryl (0.65, 1.3919), 9-anthryl (0.470, 1.2837). Selected examples of (D,p) values for several carbenes: 2-pyrimidyl (0.565, 1.7373), 4-pyrimidyl (0.555, 1.7312 (Z)), 3-pyridazinyl (0.544, 1.7066 (E), 1.7180 (Z)), 2-pyridyl (0.537, 1.7000 (E), 1.7230 (Z)), 4-quinazolyl (0.5253, 1.6737 (Z)), phenyl (0.517,1.6841), 6-phenanthridyl 21T (0.5161, 1.6575 (E), 1.6581 (Z)), (E)-2-naphthyl (0.4926, 1.6538), (E)-1-naphthyl (0.4347, 1.5973), 9-anthryl (0.3008, 1.4592).
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0035890727
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Johnson, W. T. G.; Sullivan, M. B.; Cramer, C. J. Int. J. Quantum Chem. 2001, 85, 492.
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25444528879
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To be published
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Bednarek, P.; George, L.; Wentrup, C. To be published. The calculated activation barriers for the 1,5-H shift converting 5-cyanocyclpentadiene to 1-cyanocyclopentadiene is 22.6 kcal/mol and that for conversion of 1-cyanocyclopentadiene to 2-cyanocyclopentadiene is 17.8 kcal/mol. The calculated energies of 5-, 1-, and 2-cyanocyclopentadienes are -40.3, -49.6, and -47.7 kcal/mol, respectively, relative to 1 OSS (B3LYP/6-31G*).
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