메뉴 건너뛰기




Volumn 74, Issue 16, 2009, Pages 6303-6306

Effect of ring size on the Exo/Endo selectivity of a thermal double cycloaddition of fused pyran-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

A-THERMAL; CHEMICAL EQUATIONS; N-SUBSTITUTED MALEIMIDES; PYRAN-2-ONES; REACTION CONDITIONS; RING SIZES; STARTING COMPOUNDS;

EID: 70349154635     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9011199     Document Type: Article
Times cited : (21)

References (35)
  • 15
    • 0000324982 scopus 로고
    • Endo addition involves the tendency for dienophile substituents to be so oriented in the favored transition state that they lie directly above the residual unsaturation of the diene see
    • Endo addition involves the tendency for dienophile substituents to be so oriented in the favored transition state that they lie directly above the residual unsaturation of the diene (see: Martin, J. G.; Hill, R. K. Chem. Rev. 1961, 61, 537-562).
    • (1961) Chem. Rev. , vol.61 , pp. 537-562
    • Martin, J.G.1    Hill, R.K.2
  • 16
    • 70349088859 scopus 로고    scopus 로고
    • note
    • Syn being defined as an attack from the same side of the diene system as the previously incorporated dienophile ring is located. Conversely, anti means from the other side.
  • 17
  • 20
    • 0011932271 scopus 로고    scopus 로고
    • Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany
    • (a) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
    • (2002) Microwaves in Organic Synthesis
  • 28
    • 70349119749 scopus 로고    scopus 로고
    • note
    • The C-form (cisoid) of the intermediate 4C is defined as the one where the ring of dienophile is on the same side of the diene system as the cyclooctene ring is bent to. In the T-form (transoid) one ring is on the opposite side. See Figure 1.
  • 29
    • 0038626673 scopus 로고    scopus 로고
    • et al. Revision B.03; Gaussian, Inc., Wallingford, CT
    • Frisch, M. J.; et al. et al. Gaussian 03, Revision B.03; Gaussian, Inc., Wallingford, CT, 2004.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 30
    • 70349142491 scopus 로고    scopus 로고
    • note
    • According to AM1 and PM3 calculations, exo,endo adduct 6Ce is thermodinamcally more stable than exo,exo adduct 5Ce by approximately 5 kcal/mol. Therefore, this process seems to take place under kinetic control yielding the adduct via the endo,anti attack.
  • 31
    • 70349135750 scopus 로고    scopus 로고
    • note
    • Aromatization takes place via the transfer of hydrogen to the 2e, thus forming succinic anhydride (for a related case forming substituted succinimides from maleimides, as observed previously, see ref 2d).
  • 32
    • 70349108219 scopus 로고    scopus 로고
    • note
    • Numbering sequences for compounds 5Aa, 5Bb, and 6Ca are the following: (Chemical Equation Presented)
  • 35
    • 70349134168 scopus 로고    scopus 로고
    • note
    • For the other general experimental details and characterization data for all synthesized compounds, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.