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Volumn 353, Issue 7, 2011, Pages 1071-1075

Palladium(II)-catalyzed aerobic intermolecular cyclization of acrylic acid with alkenes to α-methylene-γ-butyrolactones

Author keywords

methylene butyrolactones; homogeneous catalysis; oxidation; oxygen; palladium

Indexed keywords


EID: 79955909318     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100006     Document Type: Article
Times cited : (14)

References (61)
  • 16
    • 79955897718 scopus 로고    scopus 로고
    • 2 (15mg) in acrylic acid (2mL) saturated by oxygen decomposed rapidly to Pd(0) at the same temperature within only 5min.
    • 2 (15mg) in acrylic acid (2mL) saturated by oxygen decomposed rapidly to Pd(0) at the same temperature within only 5min.
  • 17
    • 0003441482 scopus 로고    scopus 로고
    • John Wiley & Sons, Ltd.: Chichester, U.K.
    • For recent reviews on the palladium-catalyzed aerobic oxidation, see J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Ltd.: Chichester, U.K., 2004
    • (2004) Palladium Reagents and Catalysts
    • Tsuji, J.1
  • 36
    • 79955915953 scopus 로고    scopus 로고
    • [6b] 1-acryloxy-2-octene was obtained as by-product through the π-allylpalladium intermediate. But, in our system, only traces were detected.
    • [6b] 1-acryloxy-2-octene was obtained as by-product through the π-allylpalladium intermediate. But, in our system, only traces were detected.
  • 37
    • 65249132512 scopus 로고    scopus 로고
    • It has been reported recently that a similar catalytic system is also effective for the aerobic reaction of allyl alcohol or allyl amide with vinyl ether. For examples, see Y. Kawamura, Y. Kawano, T. Matsuda, Y. Ishitobi, T. Hosokawa, J. Org. Chem. 2009, 74, 3048
    • (2009) J. Org. Chem. , vol.74 , pp. 3048
    • Kawamura, Y.1    Kawano, Y.2    Matsuda, T.3    Ishitobi, Y.4    Hosokawa, T.5
  • 50
    • 79955895548 scopus 로고    scopus 로고
    • The separation of the main exo isomer of 4 from its endo isomer is sometimes difficult by one-path column chromatography on silica gel. If necessary, the purification procedure must be repeated several times to separate them.
    • The separation of the main exo isomer of 4 from its endo isomer is sometimes difficult by one-path column chromatography on silica gel. If necessary, the purification procedure must be repeated several times to separate them.
  • 52
    • 78650392932 scopus 로고    scopus 로고
    • Palladium(II) carboxylate-catalyzed oxidation reactions in which a fine-tuned carboxylate works as an important ligand have been studied to a lesser extent. For examples, see Y. Izawa, S. S. Stahl, Adv. Synth. Catal. 2010, 352, 3223
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 3223
    • Izawa, Y.1    Stahl, S.S.2
  • 61
    • 79955892076 scopus 로고    scopus 로고
    • Now, we have succeeded in decreasing the ratio of 1-octene/acrylic acid from 10 to ca. 2 by continuous water removal from the reaction solution in a large scale-experiment. The details of these results will be reported elsewhere in the near future.
    • Now, we have succeeded in decreasing the ratio of 1-octene/acrylic acid from 10 to ca. 2 by continuous water removal from the reaction solution in a large scale-experiment. The details of these results will be reported elsewhere in the near future.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.