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Volumn 30, Issue 7, 2011, Pages 1812-1817

Synthesis and structure of gold and platinum menthyl complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; CRYSTALLOGRAPHIC STUDIES; EQUATORIAL POSITIONS; GRIGNARD REAGENT; HALIDE COMPLEXES; MAGNESIUM CHLORIDES; MENTHYL GROUPS; SPECTROSCOPIC DATA; TRANS INFLUENCE;

EID: 79953702856     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1008555     Document Type: Article
Times cited : (10)

References (67)
  • 21
    • 0034697151 scopus 로고    scopus 로고
    • Some literature procedures for preparation of menthyl Grignard reagents, including the one we used (;) explicitly describe addition of dibromoethane to activate the magnesium. The presence of bromide may affect the structure and reactivity of the reagent. For comparison, experimental procedures in refs 16b, 16c include dibromoethane, while EtBr was used in
    • Some literature procedures for preparation of menthyl Grignard reagents, including the one we used (Vedejs, E.; Donde, Y. J. Org. Chem. 2000, 65, 2337-2343) explicitly describe addition of dibromoethane to activate the magnesium. The presence of bromide may affect the structure and reactivity of the reagent. For comparison, experimental procedures in refs 16b, 16c include dibromoethane, while EtBr was used in
    • (2000) J. Org. Chem. , vol.65 , pp. 2337-2343
    • Vedejs, E.1    Donde, Y.2
  • 46
    • 0013432825 scopus 로고
    • This structure was earlier reported in. Data from the more recent structure, which gave a reduced R -factor, are included in Table 2
    • This structure was earlier reported in Gavens, P. D.; Guy, J. J.; Mays, M. J.; Sheldrick, G. M. Acta Crystallogr. 1977, 33, 137 - 139. Data from the more recent structure, which gave a reduced R -factor, are included in Table 2.
    • (1977) Acta Crystallogr. , vol.33 , pp. 137-139
    • Gavens, P.D.1    Guy, J.J.2    Mays, M.J.3    Sheldrick, G.M.4
  • 48
    • 0000670915 scopus 로고
    • 2, Cy = cyclohexyl) was also reported to decompose in solution and could not be isolated in pure form: Hackett, M.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 1449-1462
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1449-1462
    • Hackett, M.1    Whitesides, G.M.2
  • 49
    • 79953695289 scopus 로고    scopus 로고
    • note
    • 31P NMR data), but could not be purified.
  • 59
    • 33746059362 scopus 로고    scopus 로고
    • (-)-Menthyl chloride is commercially available (Aldrich), and neomenthyl chloride was prepared by a literature method
    • (-)-Menthyl chloride is commercially available (Aldrich), and neomenthyl chloride was prepared by a literature method: Ścianowski, J.; Rafiński, Z.; Wojtczak, A. Eur. J. Org. Chem. 2006, 3216-3225
    • (2006) Eur. J. Org. Chem. , pp. 3216-3225
    • Ścianowski, J.1    Rafiński, Z.2    Wojtczak, A.3
  • 60
    • 70349109218 scopus 로고    scopus 로고
    • 2-Menthene is commercially available (Aldrich), and 3-menthene was prepared by a literature method
    • 2-Menthene is commercially available (Aldrich), and 3-menthene was prepared by a literature method: Braddock, D. C.; Pouwer, R. H.; Burton, J. W.; Broadwith, P. J. Org. Chem. 2009, 74, 6042-6049
    • (2009) J. Org. Chem. , vol.74 , pp. 6042-6049
    • Braddock, D.C.1    Pouwer, R.H.2    Burton, J.W.3    Broadwith, P.4
  • 67
    • 0001248656 scopus 로고
    • Reflux of neomenthyl tosylate with 4 equiv of LiCl in acetone provided a mixture of 3-menthene and neomenthol, which was used without further workup (ref 34). Neomenthyl tosylate was synthesized following the procedure from Treatment of (+)-neomenthol (Sigma-Aldrich) with butyllithium followed by tosyl chloride gave the desired tosylate in 60% yield.
    • Reflux of neomenthyl tosylate with 4 equiv of LiCl in acetone provided a mixture of 3-menthene and neomenthol, which was used without further workup (ref 34). Neomenthyl tosylate was synthesized following the procedure from Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212-10240 Treatment of (+)-neomenthol (Sigma-Aldrich) with butyllithium followed by tosyl chloride gave the desired tosylate in 60% yield.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10212-10240
    • Giardello, M.A.1    Conticello, V.P.2    Brard, L.3    Sabat, M.4    Rheingold, A.L.5    Stern, C.L.6    Marks, T.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.