SUPPORTING INFORMATION. Polystyrene-immobilized DABCO as a highly efficient and recyclable organocatalyst for Knoevenagel condensation
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1 Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 SUPPORTING INFORMATION Polystyrene-immobilized DABCO as a highly efficient and recyclable organocatalyst for Knoevenagel condensation Da-Zhen Xu, a,b Sen Shi a and Yongmei Wang a, * b a Department of Chemistry, State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 371, People s Republic of China Fax: ; ymw@nankai.edu.cn National Pesticide Engineering Research Center (Tianjin), Nankai University, Tianjin, 371, People s Republic of China Contents Spectroscopic Data for Compounds References... 6 Spectra of compounds ( 1 H NMR, 13 C NMR)... 7
2 Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 Spectroscopic Data for Compounds 6 2-(Phenylmethylene)malononitrile (6a) 1 White solid (153 mg, yield > 99%), mp H NMR (4MHz, CD 3 ) δ: 7.57 (t, J = 8.Hz, 2H), 7.67 (t, J = 7.2Hz, 2H), 7.82 (s, 1H), 7.94 (d, J = 7.6Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 83.34, , , , 13.1, , , (2-chlorobenzylidene)malononitrile (6b) 1 White solid (187 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: (m, 1H), (m, 2H), 8.18 (d, J= 8.Hz, 1H), 8.28 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 85.78, , , , 129.6, , 13.73, 135.8, , (3-chlorobenzylidene)malononitrile (6c) 2 White solid (187 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 7.5 (t, J = 8.4Hz, 1H), (m, 1H), 7.74(s, 1H), (m, 2H). 13 C NMR (1MHz, CD 3 ) δ: 84.69, 112.6, , , 13.46, 13.92, , , , (4-chlorobenzylidene)malononitrile (6d) 1 White solid (187 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 7.52 (d, J= 8.4, 2H), 7.75 (s, 1H), 7.86 (d, J= 8.8, 2H). 13 C NMR (1MHz, CD 3 ) δ: 83.34, , , , 13.1, , , O 2 N 2-(4-nitrobenzylidene)malononitrile (6e) 1 Yellow solid (197 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 7.92 (s, 1H), 8.11 (d, J = 8.8Hz, 2H), 8.42 (d, J = 8.4Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 87.54, , , , , , 15.37, H 3 C 2-(p-tolyl) malononitrile (6f) 3 White solid (165 mg, yield 98%), m.p H NMR (4MHz, CD 3 ) δ: 2.46 (s, 3H), 7.34 (d, J = 8.4Hz, 2H), 7.73 (s, 1H), 7.81 (d, J = 8.4Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 22.6, 81.18, , 114.6, , 13.41, 13.96, ,
3 Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 MeO OMe 2-(2, 5-dimethoxybenzylidene)malononitrile (6g) 4 White solid (212 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 3.81 (s, 3H), 3.88 (s, 3H), 6.93 (d, J = 9.2Hz, 1H), 7.17 (dd, J 1 = 3.2Hz, J 2 = 9.2Hz, 1H), 7.72 (d, J = 2.8Hz, 1H), 8.28 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 55.88, 56.35, 8.95, , , , , 12.14, 124.3, , , ((naphthalen-1-yl)methylene)malononitrile (6h) 5 White solid (22 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: (m, 3H), 7.99 (d, J = 8.8Hz, 2H), 8.14 (d, J = 8.4Hz, 1H), 8.3 (d, J = 7.2Hz, 1H), 8.68 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 85.16, , , , , , , 128.6, , 131.9, , , MeO 2-(4-methoxybenzylidene)malononitrile (6i) 6 White solid (182 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 3.95 (s, 3H), 7.4 (d, J = 8.8Hz, 2H), 7.68 (s, 1H), 7.94 (d, J = 8.8Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 55.86, 78.52, , , , 124.4, , , ((E)-3-phenylallylidene)malononitrile (6j) 1 Yellow solid (179 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: (m, 2H), (m, 3H), (m, 3H). 13 C NMR (1MHz, CD 3 ) δ: 82.94, , , , 129.1, , , , 15.55, O 2-((furan-2-yl)methylene)malononitrile (6k) 7 Brown solid (143 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 6.75 (m, J = 2.Hz, 1H), 7.38 (d, J = 2.4Hz, 1H), 7.55 (s, 1H), 7.84 (s. 1H). 13 C NMR (1MHz, CD 3 ) δ: , , 114.5, , , 148.1, S 2-((thiophen-2-yl)methylene)malononitrile (6l) 8 Brown solid (159 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 7.28 (dd, J 1 = 4. Hz,
4 Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 J 2 = 5.2 Hz, 1H), 7.82 (d, J = 4. Hz, 1H), 7.89 (s, 2H). 13 C NMR (1MHz, CD 3 ) δ: 78.23, 113.2, , 129.9, , 137.4, , CO 2 Et O 2 N (E)-ethyl 2-cyano-3-(4-nitrophenyl)acrylate (6n) 9 Yellow solid (244 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 1.42 (t, J = 6.8Hz, 3H), 4.43 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 8.14 (d, J = 8.8Hz, 2H), 8.31 (s, 1H), 8.35 (d, J = 8.8Hz). 13 C NMR (1MHz, CD 3 ) δ: 14.12, 63.36, 17.37, , , , , , , CO 2 Et MeO (E)-ethyl 2-cyano-3-(4-methoxyphenyl)acrylate (6o) 9 White solid (224 mg, yield 97%), m.p H NMR (4MHz, CD 3 ) δ: 1.39 (t, J = 7.2Hz, 3H), 3.89 (s, 3H), 4.36 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 6.99 (d, J = 8.8Hz, 2H), 8. (d, J = 8.8Hz, 2H), 8.17 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 14.21, 55.64, 62.44, 99.32, , , , , 154.4, , CO 2 Et (E)-ethyl 3-(2-chlorophenyl)-2-cyanoacrylate (6p) 3 White solid (233 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 1.41 (t, J = 7.2Hz, 3H), 4.41 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 7.4 (t, J = 7.2Hz, 1H), (m, 2H), 8.23 (d, J = 8.Hz, 1H), 8.68 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 14.14, 62.96, 16.16, , , , 13.34, , , , CO 2 Et (E)-ethyl 3-(3-chlorophenyl)-2-cyanoacrylate (6q) 1 White solid (233 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 1.4 (t, J = 7.2Hz, 3H), 4.39 (q, J 1 = 6.8Hz, J 1 = 14.Hz, 2H), 7.45 (t, J = 8.Hz, 1H), 7.53 (d, J = 8.4Hz, 1H), (m, 2H), 8.18 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 14.15, 63., 14.67, , , 13.56, 13.84, 133.7, , , CO 2 Et (E)-ethyl 3-(4-chlorophenyl)-2-cyanoacrylate (6r) 9 White solid (233 mg, yield 99%), m.p H NMR (4MHz, CD 3 ) δ: 1.4 (t, J = 7.2Hz, 3H), 4.39 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 7.48 (d, J = 8.4Hz, 2H), 7.94 (d, J = 8.8Hz, 2H), 8.2 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 14.16, 62.9, 13.48, , , , , , ,
5 Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 CO 2 Et Ethyl 2-cyano-2-cyclohexylideneacetate (8a) 9 Colourless liquid (174 mg, yield 9%). 1 H NMR (4MHz, CD 3 ) δ: 1.34 (t, J = 7.2Hz, 3H), (m, 6H), 2.66 (t, J = 6.4Hz, 2H), 2.98 (t, J = 6.4Hz, 2H), 4.27 (q, J 1 = 7.2Hz, J 2 = 14Hz, 2H). NMR (1MHz, CD 3 ) δ: 14.8, 25.64, 28.26, 28.59, 31.57, 36.91, 61.71, 12.1, , 162.1, CO 2 Et Ethyl 2-(4-tert-butylcyclohexylidene)-2-cyanoacetate (8b) 11 Pale solid (232 mg, yield 93%), m.p H NMR (4MHz, CD 3 ) δ:.92 (s, 9H), 1.34 (t, J = 7.2Hz, 3H), (m, 3H), (m, 3H), (m, 3H), 4.27 (t, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 14.9, 27.46, 29.12, 32.46, 36.68, 41.32, 46.69, 61.69, 11.78, , 162.1, CO 2 Et Ethyl 2-cyano-2-(4-phenylcyclohexylidene)acetate (8c) 12 Pale solid (24 mg, yield 89%), m.p H NMR (4MHz, CD 3 ) δ: 1.35 (t, J = 7.2Hz, 3H), (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 1H), 4.29 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), (m, 3H), 7.3 (t, J = 7.2Hz, 2H). 13 C NMR (1MHz, CD 3 ) δ: 14.12, 31.13, 34.91, 36.57, 43.39, 61.89, 12.75, , , , , , , CO 2 Et NO 2 Ethyl 2-cyano-3-(3-nitrophenyl)but-2-enoate (8d) 13 Yellow solid (169 mg, yield 65%), m.p H NMR (4MHz, CD 3 ) δ: 1.33 (t, J = 7.2Hz, 3H), 2.7 (s, 3H), 4.28 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 7.7 (t, J = 7.6Hz, 1H), 8.3 (d, J = 8.Hz, 1H), 8.43 (d, J = 8.4Hz, 1H), 8.78 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 13.98, 24.77, 26.76, 63.2, , , , , , , , cyclohexylidenemalononitrile (8e) 7 Colourless liquid (145 mg, yield 99%). 1 H NMR (4MHz, CD 3 ) δ: (m, 6H), (m, 4H). 13 C NMR (1MHz, CD 3 ) δ: 24.99, 27.96, 31.19, 34.75, 82.37, ,
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