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Volumn 10, Issue 18, 2008, Pages 3993-3996

Synthesis and application of alkenylstannanes derived from base-sensitive cyclopropenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPROPANE DERIVATIVE; CYCLOPROPENE; STANNANE; TIN DERIVATIVE;

EID: 55249125797     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801486v     Document Type: Article
Times cited : (11)

References (46)
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    • Baird, M. S. Cydopropenes: Transformations (Houben-Weyl); Thieme: Stuttgart, Germany, 1997; E17d/2, pp 2781-2790.
    • (b) Baird, M. S. Cydopropenes: Transformations (Houben-Weyl); Thieme: Stuttgart, Germany, 1997; Vol. E17d/2, pp 2781-2790.
  • 8
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    • For recent, selected examples of investigations into the reactivity of cyclopropenes, see: a
    • For recent, selected examples of investigations into the reactivity of cyclopropenes, see: (a) Alnasleh, B. K.; Sherrill, W. M.; Rubin, M. Org. Lett. 2008, 10, 3231-3234.
    • (2008) Org. Lett , vol.10 , pp. 3231-3234
    • Alnasleh, B.K.1    Sherrill, W.M.2    Rubin, M.3
  • 18
    • 33746862167 scopus 로고    scopus 로고
    • For selected reviews of the Stille reaction, see: a
    • For selected reviews of the Stille reaction, see: (a) de Souza, M. V. N. Curr. Org. Synth. 2006, 3, 313-326.
    • (2006) Curr. Org. Synth , vol.3 , pp. 313-326
    • de Souza, M.V.N.1
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    • 61349187399 scopus 로고    scopus 로고
    • de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim, Chapter 3
    • (c) Mitchell, T. N. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 3.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
    • Mitchell, T.N.1
  • 26
    • 61349092050 scopus 로고    scopus 로고
    • For Stille reactions of stannylcyclopropenes, see ref 6c
    • For Stille reactions of stannylcyclopropenes, see ref 6c.
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    • 33745223065 scopus 로고    scopus 로고
    • For the use of similar conditions in the trifluoromethylation of aldehydes, see
    • For the use of similar conditions in the trifluoromethylation of aldehydes, see: Mizuta, S.; Shibata, N.; Ogawa, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Chem. Commun. 2006, 2575-2577.
    • (2006) Chem. Commun , pp. 2575-2577
    • Mizuta, S.1    Shibata, N.2    Ogawa, S.3    Fujimoto, H.4    Nakamura, S.5    Toru, T.6
  • 38
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    • 3 is not understood at this time.
    • 3 is not understood at this time.
  • 40
    • 0141785188 scopus 로고    scopus 로고
    • a of ∼30, enabling metalation with strong bases much in the same fashion as terminal alkynes. See: Fattahi, A.; McMarthy, R. E.; Ahmad, M. R.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 11746-11750.
    • a of ∼30, enabling metalation with strong bases much in the same fashion as terminal alkynes. See: Fattahi, A.; McMarthy, R. E.; Ahmad, M. R.; Kass, S. R. J. Am. Chem. Soc. 2003, 125, 11746-11750.
  • 41
    • 33646928316 scopus 로고    scopus 로고
    • For a a study of the effect of substituents at the 3-position on the HOMO and LUMO energies of cyclopropenes, see: Diev, V. V.; Kostikov, R. R.; Gleiter, R.; Molchanov, A. P. J. Org. Chem. 2006, 71, 4066-4077.
    • For a a study of the effect of substituents at the 3-position on the HOMO and LUMO energies of cyclopropenes, see: Diev, V. V.; Kostikov, R. R.; Gleiter, R.; Molchanov, A. P. J. Org. Chem. 2006, 71, 4066-4077.
  • 43
    • 61349115267 scopus 로고    scopus 로고
    • Iodocyclopropene 3 was stable and could be purified by column chromatography without noticeable decomposition.
    • Iodocyclopropene 3 was stable and could be purified by column chromatography without noticeable decomposition.
  • 45
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    • For a useful alternative preparation of these types of compounds, see
    • For a useful alternative preparation of these types of compounds, see: Chuprakov, S.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 3714-3715.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 3714-3715
    • Chuprakov, S.1    Rubin, M.2    Gevorgyan, V.3
  • 46
    • 61349174351 scopus 로고    scopus 로고
    • In the absence of further experiments, speculation about the mechanism of these reactions would be premature at this stage
    • In the absence of further experiments, speculation about the mechanism of these reactions would be premature at this stage.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.