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Volumn , Issue 8, 2007, Pages 1314-1316

Rhodium-catalyzed reaction of diazoacetates, thiols and azodicarboxylates: An unusual 1,2-aza shift from a sulfonium ylide

Author keywords

Diazo compounds; N,S ketals; One pot reaction; Rearrangement reaction; Sulfonium ylides

Indexed keywords

ACETAL DERIVATIVE; ACETIC ACID DERIVATIVE; AZODICARBOXYLATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAZOACETATE DERIVATIVE; DIRHODIUM ACETATE; RHODIUM; SULFONIUM DERIVATIVE; SULFONIUM YLIDE; THIOL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

EID: 34249787039     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977454     Document Type: Article
Times cited : (7)

References (31)
  • 4
    • 0022897055 scopus 로고    scopus 로고
    • For examples of [1,2] Stevens rearrangement of sulfonium ylides derived from metal carbenoids, see: (a) Kametani, T, Yukawa, H, Honda, T. J. Chem. Soc, Chem. Commun. 1986, 651
    • For examples of [1,2] Stevens rearrangement of sulfonium ylides derived from metal carbenoids, see: (a) Kametani, T.; Yukawa, H.; Honda, T. J. Chem. Soc., Chem. Commun. 1986, 651.
  • 7
    • 27544467423 scopus 로고    scopus 로고
    • For examples of [2,3]-sigmatropic rearrangement of ammonium ylides derived from metal carbenoids, see: (a) Ma, M, Peng, L. L, Li, C. K, Zhang, X, Wang, J. B. J. Am. Chem. Soc. 2005, 127, 15016
    • For examples of [2,3]-sigmatropic rearrangement of ammonium ylides derived from metal carbenoids, see: (a) Ma, M.; Peng, L. L.; Li, C. K.; Zhang, X.; Wang, J. B. J. Am. Chem. Soc. 2005, 127, 15016.
  • 29
    • 34249818878 scopus 로고    scopus 로고
    • Crystal Structure Data for 4h. C22H26N 2O7S, Mw, 462.51, colorless, Triclinic, P1, a, 10.343 (2, b, 10.796 (2, c, 11.630 (2) Å, α, 106.74 (2)°, β, 102.61 (2)°, γ, 101.02 (2)°, V, 1167.93 (46) Å, Z, 2, T, 287 (2) K, ρcalcd, 1.315 Mg·m-3, F(000, 488, λ, 0.71073 Å, μ, 0.183 mm-1, GOF, 0.977, R(F, 0.0435 and wR(F)2, 0.1061 for 4930 observed reflections, I > 4σ, 1.91° < c < 25.50°. CCDC 299823 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax +44 (1223)336033; or deposit@ccdc.cam.ac.uk
    • -1, GOF = 0.977, R(F) = 0.0435 and wR(F)2 = 0.1061 for 4930 observed reflections, I > 4σ, 1.91° < c < 25.50°. CCDC 299823 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax +44 (1223)336033; or deposit@ccdc.cam.ac.uk].
  • 30
    • 33747175967 scopus 로고    scopus 로고
    • A similar ring-expansion N-shift of sulfonium ylide was reported: Crow, W. D.; Gosney, I.; Ormiston, R. A. J. Chem. Soc., Chem. Commun. 1983, 643.
    • A similar ring-expansion N-shift of sulfonium ylide was reported: Crow, W. D.; Gosney, I.; Ormiston, R. A. J. Chem. Soc., Chem. Commun. 1983, 643.
  • 31
    • 34249803940 scopus 로고    scopus 로고
    • Typical Procedure for the Reaction of Diazo Compounds with Thiols and DEAD To a refluxing CH2Cl2 (8 mL) solution of Rh 2(OAc)4 (2.7 mg, 1 mol, benzenethiol 2a (66.0 mg, 0.60 mmol) and DEAD (143.6 mg, 0.83 mmol) under argon atmosphere was added methyl phenyl diazoacetate (1b, 96 mg, 0.55 mmol) in CH 2Cl2 (4 mL) over 1 h via a syringe pump. After completion of the addition, the reaction mixture was cooled to r.t. Then, the solvent was removed. The crude product was purified by flash chromatography on silica gel by using 20% EtOAc-light PE as eluent to give a white solid 4a in 70% yield. Methyl 2-(N,N′-Dicarboethoxyhydrazinyl)-2- phenyl-2-(phenylthio)acetate (4a) Rf, 0.22 (30% EtOAc-light PE, mp 126.5-1284°C. 1H NMR (300 MHz, CDCl 3, δ, 8.08 (d, J, 7.2 Hz, 2 H, 7.20-7.39 (m, 8 H, 6.51 s, 1 H, 4.27-4.3
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.