메뉴 건너뛰기




Volumn 70, Issue 20, 2005, Pages 7947-7955

Different behavior of nitrenes and carbenes on photolysis and thermolysis: Formation of azirine, ylidic cumulene, and cyclic ketenimine and the rearrangement of 6-phenanthridylcarbene to 9-phenanthrylnitrene

Author keywords

[No Author keywords available]

Indexed keywords

INFRARED SPECTROSCOPY; MATRIX ALGEBRA; PARAMAGNETIC RESONANCE; PHOTOLYSIS;

EID: 25444524624     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050898g     Document Type: Article
Times cited : (39)

References (51)
  • 8
    • 0000430416 scopus 로고
    • Abramovitch, R. A., Ed.; Plenum Press: New York, Chapter 4
    • (b) Wentrup, C. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; Vol 1, Chapter 4, p 263f.
    • (1980) Reactive Intermediates , vol.1
    • Wentrup, C.1
  • 9
    • 0002464723 scopus 로고
    • Scriven, E. F. V., Ed.; Academic Press: New York, Chapter 8
    • (c) Wentrup, C. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: New York, 1984; Chapter 8, p 395 f.
    • (1984) Azides and Nitrenes
    • Wentrup, C.1
  • 10
    • 0001343262 scopus 로고
    • 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.
    • (1972) Helv. Chim. Acta , vol.55 , pp. 2633
    • Wentrup, C.1    Thetaz, C.2    Mayor, C.3
  • 21
    • 25444464549 scopus 로고    scopus 로고
    • The University of Queensland, Brisbane, Australia. Unpublished results
    • (a) Bednarek, P.; Kvaskoff, D.; Wentrup, C. The University of Queensland, Brisbane, Australia. Unpublished results, 2004-2005.
    • (2004)
    • Bednarek, P.1    Kvaskoff, D.2    Wentrup, C.3
  • 22
    • 25444434008 scopus 로고    scopus 로고
    • Ph.D. Thesis, The University of Queensland, Brisbane, Australia
    • (b) Kvaskoff, D. Ph.D. Thesis, The University of Queensland, Brisbane, Australia, 2005.
    • (2005)
    • Kvaskoff, D.1
  • 23
    • 25444451499 scopus 로고    scopus 로고
    • note
    • (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).
  • 28
    • 25444528879 scopus 로고    scopus 로고
    • To be published
    • 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*).
    • Bednarek, P.1    George, L.2    Wentrup, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.