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Volumn 7, Issue 21, 2001, Pages 4723-4729

2- and 3-haloalkoxy fischer carbene complexes of chromium as synthons for either hydroxycyclopropanation or oxaspirocyclopropanation of alkenes

Author keywords

Alkenes; Carbene complexes; Cyclopropanation; Hydroxycyclopropanation; Lithiation; Oxaspirocyclopropanation

Indexed keywords

HALOGEN COMPOUNDS; LITHIUM; OLEFINS;

EID: 0035813664     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20011105)7:21<4723::AID-CHEM4723>3.0.CO;2-V     Document Type: Article
Times cited : (20)

References (61)
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    • For a pathway involving C-C bond cleavage with metal carbonyl formation, see: b) G. Erker, F. Sosna, Organometallics 1990, 9, 1949.
    • (1990) Organometallics , vol.9 , pp. 1949
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  • 9
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    • The formation of bicyclic cyclopropanols in very low yield by interaction at room temperature of (ethoxy)(γ,δ-alkenyl)carbene complexes of tungsten with N-methyldihydropyridine has been tentatively explained through an intramolecular cyclopropanation of the double bond by an in situ generated N-methylpyridinium oxycarbene complex: H. Rudler, A. Parlier, T. Durand-Réville, B. Martín-Vaca, M. Audouin, E. Garrier, V. Certal, J. Vaissermann, Tetrahedron 2000, 56, 5001.
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    • Rudler, H.1    Parlier, A.2    Durand-Réville, T.3    Martín-Vaca, B.4    Audouin, M.5    Garrier, E.6    Certal, V.7    Vaissermann, J.8
  • 29
    • 0006598561 scopus 로고    scopus 로고
    • note
    • Alternatively, these carbene complexes can be prepared from pentacarbonyl[1-[(tetramethylammonio)oxy]ethylidene]chromium by the acylation/haloalcohol exchange/benzaldehyde condensation sequence (see Experimental Section).
  • 30
    • 0001024887 scopus 로고
    • and ref. [9c]
    • For compounds containing the tetrahydrofuran-2-spiro-1′-cyclopropane ring system, see: A. de Meijere, I. Erden, W. Weber, D. Kaufmann, J. Org. Chem. 1988, 53, 152 and ref. [9c].
    • (1988) J. Org. Chem. , vol.53 , pp. 152
    • De Meijere, A.1    Erden, I.2    Weber, W.3    Kaufmann, D.4
  • 31
    • 0006598562 scopus 로고
    • For compounds containing the tetrahydropyran-2-spiro-1′-cyclopropane ring system, see for example: A. Vasella, C. A. A. Waldraff, Helv. Chim. Acta 1991, 74, 585 and references therein.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 585
    • Vasella, A.1    Waldraff, C.A.A.2
  • 32
    • 0006628403 scopus 로고    scopus 로고
    • note
    • The one-pot oxaspirocyclopropanation reaction was examined with carbene complex 1a and cyclohexene. After heating in THF at 120°C for 1 h, either two or four equivalents of Li-naphthalene were added at -78°C and the mixtures stirred for 15 min or 2 h, respectively. Final hydrolysis at -78°C for each experiment provided a mixture of 2-chloroethoxycyclopropane 4 a (major product) and oxaspyrocyclopropane 8a (always as a minor component).
  • 38
    • 0006598563 scopus 로고
    • In addition, the tendency of the 5-hexen-1-yl radical to cyclize to the cyclopentylmethyl radical is well documented: c) R. C. Lamb, P. W. Ayers, M. K. Toney, J. F. Garst, J. Am. Chem. Soc. 1966, 88, 4261 and references therein.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4261
    • Lamb, R.C.1    Ayers, P.W.2    Toney, M.K.3    Garst, J.F.4
  • 39
    • 0006612542 scopus 로고    scopus 로고
    • The preference for exo-cyclization of 6-hepten-1-yl radicals is known: R. A. Batey, D. V. Smil, Angew. Chem. 1999, 111, 1914;
    • (1999) Angew. Chem. , vol.111 , pp. 1914
    • Batey, R.A.1    Smil, D.V.2
  • 40
    • 0033553811 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 1798. See also ref. [16b].
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1798
  • 50
    • 0006570654 scopus 로고
    • We have observed that cyclopropanols 13-16 are unstable and upon standing even under nitrogen and when refrigerated (8-10°C), they slowly decompose to a mixture of carbonyl-containing products. Thermal isomerization of tertiary cyclopropanols to ketones has been described: a) J. T. Groves, K. W. Ma, Tetrahedron Lett. 1974, 909;
    • (1974) Tetrahedron Lett. , pp. 909
    • Groves, J.T.1    Ma, K.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.