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Volumn 45, Issue 7, 2004, Pages 1495-1498

Samarium(II)-induced ring-expansion reaction of 1,2- cyclobutanedicarboxylates to produce cyclopentanones

Author keywords

Cyclobutanes; Cyclopentanones; Radicals and radical reactions; Ring transformation; Samarium and compounds

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYCLOBUTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; HEMPA; METHANOL; SAMARIUM;

EID: 1642538422     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.047     Document Type: Article
Times cited : (7)

References (20)
  • 2
    • 85047669753 scopus 로고
    • 2-promoted ring-expansion reactions have been reported.
    • 2-promoted ring-expansion reactions have been reported. Fukuzawa S., Tsuchimoto T. Tetrahedron Lett. 36:1995;5937-5938.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5937-5938
    • Fukuzawa, S.1    Tsuchimoto, T.2
  • 6
    • 0028143797 scopus 로고
    • 2-promoted fragmentation reactions have been reported.
    • 2-promoted fragmentation reactions have been reported. Imamoto T., Hatajima T., Yoshizawa T. Tetrahedron Lett. 35:1994;7805-7808.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7805-7808
    • Imamoto, T.1    Hatajima, T.2    Yoshizawa, T.3
  • 8
    • 84914602542 scopus 로고
    • Cycloalkene
    • Cycloalkene 1 (2.0 equiv) and maleic anhydride (1.0 equiv) were used for photocycloaddition and overall yields of 2 , 3 , 4 and 5 were 13%, 35%, 43% and 37%, respectively, based on maleic anhydride. Compounds 2 and 3 can also be obtained by photocycloaddition of cyclopentene or cyclohexene with dimethyl maleate. De Mayo P., Reid S.T., Yip R.W. Can. J. Chem. 42:1964;2828-2835.
    • (1964) Can. J. Chem. , vol.42 , pp. 2828-2835
    • De Mayo, P.1    Reid, S.T.2    Yip, R.W.3
  • 14
    • 85030891346 scopus 로고    scopus 로고
    • note
    • 3): δ 25.5, 26.1, 26.8, 43.2, 45.8, 52.1, 52.3, 60.4, 169.9, 212.4.
  • 15
    • 85030900651 scopus 로고    scopus 로고
    • 1H NMR
    • 1H NMR.
  • 16
    • 85030902347 scopus 로고    scopus 로고
    • Compounds 3 , 4 and 5 were all diastereomeric mixtures but no determination was made of their respective amounts
    • Compounds 3 , 4 and 5 were all diastereomeric mixtures but no determination was made of their respective amounts.
  • 17
    • 85030897720 scopus 로고    scopus 로고
    • note
    • 3) of 22b : δ 24.7, 27.2, 35.6, 36.5, 41.3, 42.3, 45.5, 72.2 (Fig. 1 ).
  • 19
    • 85030905695 scopus 로고    scopus 로고
    • Without hydrogen peroxide treatment, reduction of the ketone in 11 occurs to give a small amount of the corresponding cyclopentanols.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.