메뉴 건너뛰기




Volumn 120, Issue 38, 1998, Pages 9949-9950

New domino sequences involving successive cleavage of carbon-carbon and carbon-oxygen bonds: Discrete product selection dictated by catalyst ligands [5]

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; CARBON; CYCLOBUTANONE DERIVATIVE; LIGAND; OXYGEN; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX; XYLENE;

EID: 0032582073     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981993s     Document Type: Letter
Times cited : (72)

References (36)
  • 25
    • 85027965918 scopus 로고    scopus 로고
    • Cyclobutanones la-d were readily prepared by [2 + 2] cycloaddition of the corresponding allylic ethers with dichloroketene and the subsequent dechlorination with zinc
    • Cyclobutanones la-d were readily prepared by [2 + 2] cycloaddition of the corresponding allylic ethers with dichloroketene and the subsequent dechlorination with zinc.
  • 26
    • 85027980794 scopus 로고    scopus 로고
    • 2
    • 2.
  • 27
    • 4544359160 scopus 로고
    • The details of the syntheses and crystal structures will be reported separately
    • Green, A.; Kuc, T. A.; Taylor, S. H. J. Chem. Soc. A 1971, 2334. The details of the syntheses and crystal structures will be reported separately.
    • (1971) J. Chem. Soc. A , pp. 2334
    • Green, A.1    Kuc, T.A.2    Taylor, S.H.3
  • 28
    • 85028018282 scopus 로고    scopus 로고
    • Monitoring the reaction by capillary GC revealed that decarbonylated cyclopropane 8a was formed as a sole side product (~4.5%), and formation of cyclopentanone 7a was not observed
    • Monitoring the reaction by capillary GC revealed that decarbonylated cyclopropane 8a was formed as a sole side product (~4.5%), and formation of cyclopentanone 7a was not observed.
  • 29
    • 85027966694 scopus 로고    scopus 로고
    • Whereas a less substituted a-bond is cleaved in the hydrogenolysis of an ordinary cyclobutanone.4b the more substituted a-bond is cleaved in the present case. It is likely that coordination of the ether linkage to rhodium facilitates insertion into the more substituted but proximate a-bond
    • Whereas a less substituted a-bond is cleaved in the hydrogenolysis of an ordinary cyclobutanone.4b the more substituted a-bond is cleaved in the present case. It is likely that coordination of the ether linkage to rhodium facilitates insertion into the more substituted but proximate a-bond.
  • 31
    • 85027965923 scopus 로고    scopus 로고
    • Decarbonylated cyclopropane 8a was observed by GC as the only side product (~12%)
    • Decarbonylated cyclopropane 8a was observed by GC as the only side product (~12%).
  • 34
    • 85027996755 scopus 로고    scopus 로고
    • Alternatively, recyclization of 4 by addition of the Rh-C linkage across the C—C double bond in a 5-endo mode followed by reductive elimination forming a C-O bond is also conceivable for the production of 7a
    • Alternatively, recyclization of 4 by addition of the Rh-C linkage across the C—C double bond in a 5-endo mode followed by reductive elimination forming a C-O bond is also conceivable for the production of 7a.
  • 35
    • 85028000120 scopus 로고    scopus 로고
    • Neither 5a nor 7a was detected by GC
    • Neither 5a nor 7a was detected by GC.
  • 36
    • 85027987709 scopus 로고    scopus 로고
    • The reaction of lb catalyzed by the dppb complex 2c afforded the corresponding decarbonylated cyclopropane 8b in 93% yield, being in accordance with other examples
    • The reaction of lb catalyzed by the dppb complex 2c afforded the corresponding decarbonylated cyclopropane 8b in 93% yield, being in accordance with other examples.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.