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Volumn 4, Issue 23, 2006, Pages 4307-4318

Synthesis and Claisen rearrangement of bridged bicyclic enol ethers of relevance to the course of ketene s-cis-diene cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; INORGANIC ACIDS; OLEFINS; REACTION KINETICS; SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 33750980400     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b611311g     Document Type: Article
Times cited : (12)

References (47)
  • 7
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    • For a recent detailed investigation of the ketene-cyclopentadiene system which requires a re-casting of the results reported in references 1 and 5 see:
    • J. Marchand-Brynaert L. Ghosez Tetrahedron Lett. 1974 377
    • (1974) Tetrahedron Lett. , pp. 377
    • Marchand-Brynaert, J.1    Ghosez, L.2
  • 8
    • 33745055198 scopus 로고    scopus 로고
    • There seems to be little or no precedent for the 2-oxabicyclo[2.2.1]hep- 5-en-3-one system except for an unusual simple bicyclic enol:
    • B. R. Ussing C. Hang D. A. Singleton J. Am. Chem. Soc. 2006 128 7594
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 7594
    • Ussing, B.R.1    Hang, C.2    Singleton, D.A.3
  • 17
  • 19
    • 0034693312 scopus 로고    scopus 로고
    • The slow addition of LDA to a cold (-78 °C) THF solution of chloroform and the requisite aldehyde (Schemes 5 & 6) is based on
    • V. K. Aggarwal A. Mereu J. Org. Chem. 2000 65 7211
    • (2000) J. Org. Chem. , vol.65 , pp. 7211
    • Aggarwal, V.K.1    Mereu, A.2
  • 25
    • 13444263819 scopus 로고    scopus 로고
    • Cycloreversion of the adduct of diethyl ketomalonate and cyclopentadiene is complete at temperatures above ca. -30 °C:
    • K. C. Nicolaou H. Xu M. Wartmann Angew. Chem., Int. Ed. 2005 44 756
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 756
    • Nicolaou, K.C.1    Xu, H.2    Wartmann, M.3
  • 29
    • 33750973306 scopus 로고    scopus 로고
    • DPhil Thesis, Oxford, Review
    • For details of the preparation of bicycles 9-13 see T. G. Fowler, DPhil Thesis, Oxford, 2005
    • (2005)
    • Fowler, T.G.1
  • 32
    • 4644245555 scopus 로고    scopus 로고
    • The use of added LiCl to promote the cross-coupling of vinyl triflates with organostannanes was first reported in:
    • P. Espinet A. M. Echavarren Angew. Chem., Int. Ed. 2004 43 4704
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4704
    • Espinet, P.1    Echavarren, A.M.2
  • 33
    • 0000725865 scopus 로고
    • In these cases a small quantity of starting enol ether was present at the end of the specified time, the reactions being stopped in order to maximise the yield of cyclobutanone products. Free cyclohexadiene, arising from cycloreversion, was observed in the NMR spectra in increasing quantities as the reaction time was extended; this was the major contributor to the lowered yields, particularly in table entries 4 and 5. There was no clear evidence in these spectra of the presumably co-formed arylketenes; these are expected to oligomerise under the reaction conditions
    • W. J. Scott G. T. Crisp J. K. Stille J. Am. Chem. Soc. 1984 106 4630
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4630
    • Scott, W.J.1    Crisp, G.T.2    Stille, J.K.3
  • 40
    • 0000130570 scopus 로고
    • For a summary of substituent effects on the rate of Claisen rearrangements and a discussion of mechanistic interpretations arising from these data see:
    • H. L. Goering R. R. Jacobson J. Am. Chem. Soc. 1958 80 3277
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3277
    • Goering, H.L.1    Jacobson, R.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.