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Volumn 37, Issue 10, 1996, Pages 1523-1526

Reversible Friedel-Crafts acylations of 3-alkyl-1-(phenylsulfonyl)pyrroles: Application to the synthesis of an ant trail pheromone

Author keywords

[No Author keywords available]

Indexed keywords

PHEROMONE; PYRROLE DERIVATIVE;

EID: 0030005638     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00098-6     Document Type: Article
Times cited : (10)

References (36)
  • 6
    • 0342996701 scopus 로고
    • (b) Pearson, R. G. Science 1966, 151, 172-177.
    • (1966) Science , vol.151 , pp. 172-177
    • Pearson, R.G.1
  • 11
    • 85030188098 scopus 로고    scopus 로고
    • unpublished results
    • Ketcha, D. M., unpublished results.
    • Ketcha, D.M.1
  • 15
    • 0342946647 scopus 로고
    • For examples of rearrangement processes of pyrroles, see: (a) Kakushima, M.; Frenette, R. J. Org. Chem. 1984, 49, 2025-2027.
    • (1984) J. Org. Chem. , vol.49 , pp. 2025-2027
    • Kakushima, M.1    Frenette, R.2
  • 22
    • 0001534481 scopus 로고
    • For previous syntheses of methyl 4-methylpyrrole-2-carboxylate, see: (a) Rapoport, H.; Bordner, J. J. Org. Chem. 1964, 29, 2727-2731
    • (1964) J. Org. Chem. , vol.29 , pp. 2727-2731
    • Rapoport, H.1    Bordner, J.2
  • 31
    • 0842341771 scopus 로고
    • a,b all-valence-electron molecular orbital calculations of total energy indicate that the 3,5-form is more stable than the 2,3-form by ca. 1.2 kcal/mol. Differences in overall stabilization arise because the 3-methyl group forces the 2-acetyl substituent to assume energetically unfavorable orientations: (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 32
    • 85030191077 scopus 로고    scopus 로고
    • Quantum Chemistry Program Exchange, Indiana Univ., Bloomington, IN 47405
    • (b) Stewart, J. J. P., MOPAC, QCPE Program 445, ver. 6.0, Quantum Chemistry Program Exchange, Indiana Univ., Bloomington, IN 47405.
    • MOPAC, QCPE Program 445, Ver. 6.0
    • Stewart, J.J.P.1
  • 36
    • 85030197189 scopus 로고    scopus 로고
    • note
    • 13C NMR δ 161.6, 121.3, 120.9, 116.4, 51.3, 11.6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.