메뉴 건너뛰기




Volumn 6, Issue 12, 2004, Pages 2059-2062

α,5-didehydro-3-picoline diradicals from skipped azaenediynes: Computational and trapping studies of an aza-Myers-Saito cyclization

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 3 TRI(ISOPROPYL)SILYLPROP 2 YNONE; 1,4 CYCLOHEXADIENE; 6 PHENYL 3 PICOLINE; ALKADIENE; ALLENE DERIVATIVE; ALPHA,5 DIDEHYDRO 3 PICOLINE; AMMONIUM DERIVATIVE; FLUORIDE; HETEROCYCLIC COMPOUND; IMINE; N PROPARGYLIMINE; PICOLINE DERIVATIVE; RADICAL; SILANE DERIVATIVE; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

EID: 3042837537     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049266r     Document Type: Article
Times cited : (42)

References (41)
  • 28
    • 0347052792 scopus 로고    scopus 로고
    • For theoretical studies of enyne allenes in which the central double bond is replaced with various heteroatoms see: Bui, B. H.; Schreiner, P. R. Org. Lett. 2003, 5, 4871-4874.
    • (2003) Org. Lett. , vol.5 , pp. 4871-4874
    • Bui, B.H.1    Schreiner, P.R.2
  • 30
    • 3042770678 scopus 로고    scopus 로고
    • note
    • Despite a certain lack of theoretical rigor in applying UB3LYP calculations to these open-shell singlets, we report these values for comparison with the results in the enyne allene series in refs 2a, 18, and 19. One can reach the same conclusions by comparing the triplet diradical energies.
  • 31
    • 3042770348 scopus 로고    scopus 로고
    • note
    • For the zwitterion 4a±, we find a structure lower in energy than that reported in ref 19. We note that the wave function is unstable with respect to symmetry breaking for both 4± and 5 at the B3LYP level.
  • 34
    • 3042811014 scopus 로고    scopus 로고
    • note
    • In the aza-Myers-Saito case, B3LYP/6-31G* calculations indicate that 4b± is a saddle point corresponding to the transition state for the interconversion of the two enantiomeric cyclic allenes 5b.
  • 38
    • 85088734895 scopus 로고    scopus 로고
    • note
    • +).
  • 39
    • 85088735186 scopus 로고    scopus 로고
    • note
    • 1H NMR and MS analysis. Similarly low yields of 9 were obtained from reactions in THF, which is apparently a poor hydrogen atom donor towards 4d••.
  • 40
    • 3042727834 scopus 로고    scopus 로고
    • note
    • We thank one of the reviewers for bringing this possibility to our attention.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.