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4
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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
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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.
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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.
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For metal-catalyzed S-H insertion, see: a
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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
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-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].
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33747175967
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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.
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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.
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34249803940
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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
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