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Volumn 1, Issue 1, 2002, Pages 38-44

Thermoreversible photocyclization of a pyrazolotriazole to a triazasemibullvalene: A novel electrocyclic reaction

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; PYRAZOLE DERIVATIVE; TRIAZASEMIBULLVALENE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0041409504     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b106231j     Document Type: Article
Times cited : (9)

References (37)
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    • H. Dürr and H. Bouas-Laurent (Ed.), Elsevier, Amsterdam
    • C. Schulz and H. Dürr, in Photochromism, H. Dürr and H. Bouas-Laurent (Ed.), Elsevier, Amsterdam, 1990, p. 193.
    • (1990) Photochromism , pp. 193
    • Schulz, C.1    Dürr, H.2
  • 5
    • 0038991098 scopus 로고
    • A. Hassner (Ed.), Wiley, New York
    • H. W. Heine, in Small Rings, Part 2, A. Hassner (Ed.), Wiley, New York, 1983, p. 547.
    • (1983) Small Rings , pp. 547
    • Heine, H.W.1
  • 6
    • 0000399183 scopus 로고
    • D. Klaman (Ed.), Thieme, Stuttgart
    • E. Schmitz, Houben-Weyl Meth. Org. Chem., D. Klaman (Ed.), Thieme, Stuttgart, 1992, vol. E16C, p. 678.
    • (1992) Houben-Weyl Meth. Org. Chem. , vol.E16C , pp. 678
    • Schmitz, E.1
  • 14
    • 85034333361 scopus 로고    scopus 로고
    • Benzodiazirines have been postulated as intermediates in the photochemical rearrangement of N-iminopyridinium ylides, but no direct evidence has been found for such compounds10a
    • Benzodiazirines have been postulated as intermediates in the photochemical rearrangement of N-iminopyridinium ylides, but no direct evidence has been found for such compounds10a.
  • 17
    • 0000349036 scopus 로고
    • A. Padwa (Ed.), Wiley, New York
    • R. Grashey, in 1,3 Dipolar Cycloadditions, A. Padwa (Ed.), Wiley, New York, 1984, vol. 1, p. 733.
    • (1984) 1,3 Dipolar Cycloadditions , vol.1 , pp. 733
    • Grashey, R.1
  • 19
    • 85034366393 scopus 로고    scopus 로고
    • The systematic name of compound 1b is 8H-3a,8,8a-triazacyclopent[a]indene. 1c is the corresponding 1,3-dimethyl derivative
    • The systematic name of compound 1b is 8H-3a,8,8a-triazacyclopent[a]indene. 1c is the corresponding 1,3-dimethyl derivative.
  • 30
    • 85034378276 scopus 로고    scopus 로고
    • We also attempted to calculate the excited-state electronic structure of compounds 1 by the CASPT2 method. However, this turned out to be difficult because on inclusion of higher roots in the state-averaging CASSCF procedure the nature of the first excited state changed completely from that which is obtained on averaging only the lowest two roots. Normal CASPT2 perturbation theory proved incapable of rectifying this and consequently the corresponding predictions were unsatisfactory. Note, however, that this particular difficulty with CASSCF has no bearing on the application of this procedure in the remainder of the present work
    • We also attempted to calculate the excited-state electronic structure of compounds 1 by the CASPT2 method. However, this turned out to be difficult because on inclusion of higher roots in the state-averaging CASSCF procedure the nature of the first excited state changed completely from that which is obtained on averaging only the lowest two roots. Normal CASPT2 perturbation theory proved incapable of rectifying this and consequently the corresponding predictions were unsatisfactory. Note, however, that this particular difficulty with CASSCF has no bearing on the application of this procedure in the remainder of the present work.
  • 31
    • 85034378768 scopus 로고    scopus 로고
    • The systematic name of compound 2b is: 2aH-2b,6b,6c-triazabenzo[a]cyclopropa[cd]pentalene. Compound 2c is the corresponding 1,2a-dimethyl derivative
    • The systematic name of compound 2b is: 2aH-2b,6b,6c-triazabenzo[a]cyclopropa[cd]pentalene. Compound 2c is the corresponding 1,2a-dimethyl derivative.
  • 37
    • 85034368723 scopus 로고    scopus 로고
    • 1 state averaging, whereas the latter were calculated with CASSCF wavefunctions optimized for the ground states only
    • 1 state averaging, whereas the latter were calculated with CASSCF wavefunctions optimized for the ground states only.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.