One-Pot Synthesis of Symmetric 1,7-Dicarbonyl Compounds Via. a Tandem Radical Addition - Elimination Addition Reaction
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1 S1 One-Pot Synthesis of Symmetric 1,7-Dicarbonyl Compounds Via a Tandem Radical Addition - Elimination Addition Reaction Zhongyan Huang and Jiaxi Xu* State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing , China. Fax: (+86) jxxu@mail.buct.edu.cn Contents...S1 Ananlytic data of known O-ethyl S-carbonylmethyl xanthates 1 and allyl sulfur compounds 2...S2 Copies of 1 H and 13 C NMR spectra of unknown O-ethyl S-carbonylmethyl xanthates 1...S5 Copies of 1 H and 13 C NMR spectra of unknown allylbutylsulfoxide 2d...S10 Copies of 1 H and 13 C NMR spectra of symmetric 1,7-dicarbonyl compounds 3...S11
2 S2 Ananlytic data of known O-ethyl S-carbonylmethyl xanthates 1 and allyl sulfur compounds 2 O-Ethyl S-[2-phenyl-2-oxoethyl] carbonodithioate (1a). Pale yellow solid, yield: 1.08 g, 90%, m.p o C, Lit. 1 m.p o C. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.39 (t, J = 7.1 Hz, 3H, CH 3 ), 4.63 (q, J = 7.1 Hz, 2H, CH 2 ), 4.66 (s, 2H, CH 2 ), 7.50 (t, J = 7.6 Hz, 2H, ArH), 7.61 (t, J = 7.6 Hz, 1H, ArH), 8.01 (d, J = 7.6 Hz, 2H, ArH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 43.5 (CH 2 ), 70.6 (CH 2 ), (CH), (CH), (CH), (CH), (C), (C=O), (C=S). O-Ethyl S-[2-(4-methoxyphenyl)-2-oxoethyl] carbonodithioate (1b). Pale yellow solid, yield: 1.20 g, 89%, m.p o C, Lit. 1 m.p o C. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.40 (t, J = 7.1 Hz, 3H, CH 3 ), 3.88 (s, 3H, CH 3 ), 4.62 (s, 2H, CH 2 ), 4.64 (q, J = 7.1 Hz, 2H, CH 2 ), 7.50 (d, J = 8.6 Hz, 2H, ArH), 8.01 (d, J = 8.6 Hz, 2H, ArH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 43.1 (CH 2 ), 55.2 (CH 3 ), 70.2 (CH 2 ), (CH), (C), (CH), (C), (C=O), (C=S). O-Ethyl S-(2-oxopropyl) carbonodithioate (1c). 2 Pale yellow liquid, yield: 0.81 g, 91%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.39 (t, J = 7.1 Hz, 3H, CH 3 ), 2.30 (s, 3H, CH 3 ), 3.97 (s, 2H, CH 2 ), 4.67 (q, J = 7.1 Hz, 2H, CH 2 ). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.7 (CH 3 ), 29.1 (CH 3 ), 45.9 (CH 2 ), 70.6 (CH 2 ), (C=O), (C=S). S-(3-Chloro-2-oxopropyl) O-ethyl carbonodithioate (1d). White solid 1.12 g, yield: 70%, m.p o C, Lit o C. 1 H NMR (400 MHz, CDCl 3 ) (δ, ppm) 1.43 (t, J = 7.1 Hz, 3H, CH 3 ), 4.15 (s, 2H, CH 2 ), 4.30 (s, 2H, CH 2 ), 4.64 (q, J = 7.1 Hz, 2H, CH 2 ). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6, 42.8, 47.8, 71.2, 195.6, S-(2-Ethoxyl-2-oxoethyl) O-ethyl carbonodithioate (1e). 4 Pale yellow liquid, yield: 0.92 g, 88%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.29 (t, J = 7.1 Hz, 3H, CH 3 ), 1.42 (t, J = 7.1 Hz, 3H, CH 3 ), 3.92 (s, 2H, CH 2 ), 4.22 (q, J = 7.1 Hz, 2H, CH 2 ), 4.64 (q, J = 7.1 Hz, 2H, CH 2 ). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 14.1 (CH 3 ), 37.8 (CH 2 ), 61.8 (CH 2 ), 70.5 (CH 2 ), (C=O), (C=S). O-Ethyl S-(2-phenoxy-2-oxoethyl) carbonodithioate (1f). 5 Pale yellow liquid, yield: 1.18 g, 92%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.43 (t, J = 7.1 Hz, 3H, CH 3 ), 4.13 (s, 2H, CH 2 ), 4.67 (q, J = 7.1 Hz, 2H, CH 2 ), 7.11 (d, J = 7.6 Hz, 2H, ArH), 7.23 (t, J = 7.6 Hz, 2H, ArH), 7.38 (t, J = 7.6 Hz, 2H, ArH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 37.9 (CH 2 ), 70.8 (CH 2 ), (CH), (CH), (CH), (C), (C=O), (C=S). O-Ethyl S-[2-oxo-2-(oxazolidin-2-on-3-yl)ethyl] carbonodithioate (1l). Pale yellow solid, yield: 1.11 g, 89%, m.p o C, Lit. 6 m.p. 96 o C. 1 H NMR (CDCl 3, 400
3 S3 MHz) (δ, ppm) 1.43 (t, J = 7.1 Hz, 3H, CH 3 ), 4.07 (t, J = 8.0 Hz, 2H, CH 2 ), 4.49 (t, J = 8.1 Hz, 2H, CH 2 ), 4.57 (s, 2H, CH 2 ), 4.65 (q, J = 7.1 Hz, 2H, CH 2 ). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 39.3 (CH 2 ), 42.6 (CH 2 ), 62.4 (CH 2 ), 70.6 (CH 2 ), (C=O), (C=O), (C=S). S-(Cyanomethyl) O-ethyl carbonodithioate (1m). 7 Pale yellow liquid, yield: 0.71 g, 88%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.47 (t, J = 7.1 Hz, 3H, CH 3 ), 3.89 (s, 2H, CH 2 ), 4.72 (q, J = 7.1 Hz, 2H, CH 2 ). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 13.6 (CH 3 ), 21.3 (CH 2 ), 71.5 (CH 2 ), (CN), (C=S). Allyl methylsulfone (2a). 8 Colorless liquid, yield: 10.5 g, 87%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 2.87 (s, 3H, CH 3 ), 3.74 (d, J = 7.6 Hz, 2H, CH 2 ), 5.48 (d, J = 17.2 Hz, 1H in CH 2 ), 5.52 (d, J = 10.2 Hz, 1H in CH 2 ), (m, 1H, CH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 38.9 (CH 3 ), 59.3 (CH 2 ), (CH 2 ), (CH). Allyl ethylsulfone (2b). 9 Colorless liquid, from sodium ethanesulphinate (2.50 g, 21.5 mmol), yield: 1.75 g, 60%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 1.39 (t, J = 7.1 Hz, 3H, CH 3 ), 3.00 (q, J = 7.1 Hz, 2H, CH 2 ), 3.71 (d, J = 7.6 Hz, 2H, CH 2 ), (m, 2H, CH 2 ), 5.95 (ddt, J = 14.4, 10.4, 7.6 Hz, 1H, CH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 6.4 (CH 3 ), 45.6 (CH 2 ), 56.8 (CH 2 ), (CH 2 ), (CH). Allyl phenylsulfone (2c). 10 Colorless liquid, yield: 15.6 g, 85%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 3.81 (d, J = 7.6 Hz, 2H, CH 2 ), 5.15 (d, J = 17.2 Hz, 1H in CH 2 ), 5.33 (d, J = 10.0 Hz, 1H in CH 2 ), (m, 1H, CH), 7.56 (t, J = 7.6 Hz, 2H, ArH), 7.65 (t, J = 7.6 Hz, 1H, ArH), 7.88 (d, J = 7.6 Hz, 2H, ArH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 60.8 (CH 2 ), (CH), (CH 2 ), (CH), (CH), (CH), (C). Allyl phenylsulfoxide (2e). 11 Colorless liquid, yield: 0.83 g, 50%. 1 H NMR (CDCl 3, 400 MHz) (δ, ppm) 3.52 (dd, J = 12.8, 7.6 Hz, 1H in CH 2 ), 3.58 (dd, J = 12.8, 7.6 Hz, 1H in CH 2 ), 5.16 (d, J = 17.2 Hz, 1H in CH 2 ), 5.20 (d, J = 10.0 Hz, 1H in CH 2 ), (m, 1H, CH), (m, 4H, ArH), 7.87 (d, J = 7.6 Hz, 1H, ArH). 13 C NMR (CDCl 3, 100 MHz) (δ, ppm) 60.8 (CH 2 ), (CH), (CH 2 ), (CH), (CH), (CH), (C). References 1 B. Batanero, O. Picazo and E. Barba, J. Org. Chem. 2001, 66, V. Liautard, F. Robert and Y. Landais, Org. Lett. 2011, 13, M. De Greef and S. Z. Zard, Org. Lett. 2007, 9, A. Kapat, E. Nyfeler, G. Giuffredi and P. Renaud, J. Am. Chem. Soc. 2009, 131, E. Godineau and Y. Landais, J. Am. Chem. Soc. 2007, 129, E. Bacqué, F. Pautrat and S. Z. Zard, Chem. Commun. 2002,
4 S4 7 S. Kakaei, N. Chen and J. X. Xu, Tetrahedron 2013, 69, G. C. Tsui and M. Lautens, Angew. Chem., Int. Ed. 2010, 49, R. J. Palmer and C. J. M. Stirling, J. Am. Chem. Soc. 1980, 102, G. A. Russell and L. L. Herold, J. Org. Chem. 1985, 50, K. Bahrami, M. M. Khodaei and M. Sheikh Arabi, J. Org. Chem. 2010, 75,
5 S5 Copies of 1 H and 13 C NMR spectra of unknown O-ethyl S-carbonylmethyl xanthates 1 S-[2-(4-Chlorophenoxy)-2-oxoethyl] O-ethyl carbonodithioate (1g)
6 S6 O-Ethyl S-[2-(4-nitrophenoxy)-2-oxoethyl] carbonodithioate (1h)
7 S7 S-(2-Benzyloxy-2-oxoethyl) O-ethyl carbonodithioate (1i)
8 S8 S-(2-Diphenylamino-2-oxoethyl) O-ethyl carbonodithioate (1j)
9 S9 O-Ethyl S-[2-(methanesulfonylphenylamino)-2-oxoethyl] carbonodithioate (1k)
10 S10 Copies of 1 H and 13 C NMR spectra of unknown allylbutylsulfoxide 2d Allylbutylsulfoxide (2d)
11 S11 Copies of 1 H and 13 C NMR spectra of symmetric 1,7-dicarbonyl compounds 3 S-(1,7-Dioxo-1,7-diphenylheptan)-4-yl O-ethyl carbonodithioate (3a)
12 S12 S-[1,7-Dioxo-1,7-di (4-methoxyphenyl)heptan]-4-yl O-ethyl carbonodithioate (3b)
13 S13 S-(1,7-Dioxononan)-5-yl O-ethyl carbonodithioate (3c)
14 S14 S-(1,7-Dichloro-1,7-dioxononan)-5-yl O-ethyl carbonodithioate (3d)
15 S15 S-(1,7-Diethoxyl-1,7-dioxoheptan)-4-yl O-ethyl carbonodithioate (3e)
16 S16 S-(1,7-Dioxo-1,7-diphenoxyheptan)-4-yl O-ethyl carbonodithioate (3f)
17 S17 S-[1,7-Di(4-chloro-phenoxy)-1,7-dioxoheptan]-4-yl O-ethyl carbonodithioate (3g)
18 S18 S-[1,7-Di(4-nitro-phenoxy)-1,7-dioxoheptan]-4-yl O-ethyl carbonodithioate (3h)
19 S19 S-(1,7-Dibenzyloxy-1,7-dioxoheptan)-4-yl O-ethyl carbonodithioate (3i)
20 S20 S-{[1,7-Di(diphenylamino)-1,7-dioxo]heptan}-4-yl O-ethyl carbonodithioate (3j)
21 S21 S-[1,7-Di(methanesulfonylphenylamino)-1,7-dioxoheptan]-4-yl O-ethyl carbonodithioate (3k)
22 S22 S-[1,7-Dioxo-1,7-di(2-oxooxazolidin-3-yl)heptan]-4-yl O-ethyl carbonodithioate (3l)
23 S23 S-(1,5-Dicyanopentan-3-yl) O-ethyl carbonodithioate (3m)
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