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Volumn 72, Issue 15, 2007, Pages 5938-5941

Bistrimethylsilylpropargylic ether: A versatile ambident synthon to access substituted allenyne ethers and α-substituted bispropargylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALLENYNE ETHERS; BISPROPARGYLIC ALCOHOLS; BISTRIMETHYLSILYLPROPARGYLIC ETHERS; SYNTHON;

EID: 34547094993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0709753     Document Type: Article
Times cited : (19)

References (47)
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    • We thank Prof. Jia (see ref 4) for his helpful and warning comments: a violent explosion may take place during the vacuum distillation of crude 1 if the bath temperature is over 90°C or if the viscosity of the residue is too high to permit the diffusion of heat. In that case, distillation should be stopped immediately to avoid accident
    • We thank Prof. Jia (see ref 4) for his helpful and warning comments: a violent explosion may take place during the vacuum distillation of crude 1 if the bath temperature is over 90°C or if the viscosity of the residue is too high to permit the diffusion of heat. In that case, distillation should be stopped immediately to avoid accident.
  • 16
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    • (c) Ma, S. Chem. Rev. 2005, 105, 2829-2871.
    • (2005) Chem. Rev , vol.105 , pp. 2829-2871
    • Ma, S.1
  • 22
    • 0012114207 scopus 로고
    • For preparation of allenynes catalyzed by Pd, see: a
    • For preparation of allenynes catalyzed by Pd, see: (a) Markl, G.; Attenberger, P.; Kellner, J. Tetrahedron Lett. 1988, 29, 3651-3654.
    • (1988) Tetrahedron Lett , vol.29 , pp. 3651-3654
    • Markl, G.1    Attenberger, P.2    Kellner, J.3
  • 27
    • 1942521129 scopus 로고    scopus 로고
    • For reverse Brook rearrangement, see
    • (b) For reverse Brook rearrangement, see: Tokeshi, B. K.; Tius, M. A. Synthesis 2004, 5, 786-790.
    • (2004) Synthesis , vol.5 , pp. 786-790
    • Tokeshi, B.K.1    Tius, M.A.2
  • 33
    • 34547099871 scopus 로고    scopus 로고
    • Whatever conditions used (time, temperature, equivalent of base), 3d-f yielded mostly 4d-f compared to 5d-f.
    • (a) Whatever conditions used (time, temperature, equivalent of base), 3d-f yielded mostly 4d-f compared to 5d-f.
  • 34
    • 34547094402 scopus 로고    scopus 로고
    • 5d was successfully prepared from 4d with BuLi/TMSCl (43% yield); see Supporting Information for details.
    • (b) 5d was successfully prepared from 4d with BuLi/TMSCl (43% yield); see Supporting Information for details.
  • 35
    • 34547109151 scopus 로고
    • Ph.D. Thesis, University of Strasbourg, France
    • Alayrac, C. Ph.D. Thesis, University of Strasbourg, France, 1993.
    • (1993)
    • Alayrac, C.1
  • 36
    • 34547100109 scopus 로고    scopus 로고
    • TBAF treatment was employed for 3e,f.
    • TBAF treatment was employed for 3e,f.
  • 37
    • 8344224576 scopus 로고    scopus 로고
    • Base-catalyzed isomerization of alkynes has precedent in the literature: Hopf, H. Chem. Ber. 1971, 104, 3087-3095; see also ref 12.
    • Base-catalyzed isomerization of alkynes has precedent in the literature: Hopf, H. Chem. Ber. 1971, 104, 3087-3095; see also ref 12.
  • 38
    • 34547100589 scopus 로고    scopus 로고
    • n-BuLi was used for all of the reactions. s-BuLi gave the same results (products and yields).
    • n-BuLi was used for all of the reactions. s-BuLi gave the same results (products and yields).
  • 39
    • 34547111337 scopus 로고    scopus 로고
    • Addition of the electrophile prior to addition of BuLi (internal quench) gave the same alkylation results
    • Addition of the electrophile prior to addition of BuLi (internal quench) gave the same alkylation results.
  • 40
    • 34547092737 scopus 로고    scopus 로고
    • These low yields are due to the instabilities of 6d and 8d.
    • These low yields are due to the instabilities of 6d and 8d.
  • 42
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    • (b) Ho, T.-S. Chem. Rev. 1975, 75, 1-20.
    • (1975) Chem. Rev , vol.75 , pp. 1-20
    • Ho, T.-S.1
  • 43
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    • HSAB rationalization and inconsistent reactivity were previously reported for lithiated allenes: (a) Creary, X. J. Am. Chem. Soc. 1977, 99, 7632-7639.
    • HSAB rationalization and inconsistent reactivity were previously reported for lithiated allenes: (a) Creary, X. J. Am. Chem. Soc. 1977, 99, 7632-7639.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.