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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: +86 22 235 2654; e-mail: ymw@nankai.edu.cn National Pesticide Engineering Research Center (Tianjin), Nankai University, Tianjin, 371, People s Republic of China Contents Spectroscopic Data for Compounds 6... 2 References... 6 Spectra of compounds ( 1 H NMR, 13 C NMR)... 7

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. 83-84. 1 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, 112.38, 113.48, 129.29, 13.1, 131.88, 141.18, 158.35. 2-(2-chlorobenzylidene)malononitrile (6b) 1 White solid (187 mg, yield 99%), m.p. 94. 1 H NMR (4MHz, CD 3 ) δ: 7.43-7.48 (m, 1H), 7.53-7.59 (m, 2H), 8.18 (d, J= 8.Hz, 1H), 8.28 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 85.78, 111.94, 113.25, 127.82, 129.6, 129.52, 13.73, 135.8, 136.36, 156.1. 2-(3-chlorobenzylidene)malononitrile (6c) 2 White solid (187 mg, yield 99%), m.p. 113-115. 1 H NMR (4MHz, CD 3 ) δ: 7.5 (t, J = 8.4Hz, 1H), 7.59-7.61 (m, 1H), 7.74(s, 1H), 7.83-7.85 (m, 2H). 13 C NMR (1MHz, CD 3 ) δ: 84.69, 112.6, 113.23, 128.37, 13.46, 13.92, 132.32, 134.39, 135.82, 158.25. 2-(4-chlorobenzylidene)malononitrile (6d) 1 White solid (187 mg, yield 99%), m.p. 164-165. 1 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, 112.38, 113.48, 129.29, 13.1, 131.88, 141.18, 158.35. O 2 N 2-(4-nitrobenzylidene)malononitrile (6e) 1 Yellow solid (197 mg, yield 99%), m.p. 161-162. 1 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, 111.63, 112.66, 124.67, 131.35, 135.82, 15.37, 156.93. H 3 C 2-(p-tolyl) malononitrile (6f) 3 White solid (165 mg, yield 98%), m.p. 133-134. 1 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, 112.91, 114.6, 128.48, 13.41, 13.96, 146.44, 159.83.

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. 19-11. 1 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, 111.17, 112.85, 113.24, 114.38, 12.14, 124.3, 153.47, 153.79, 154.14. 2-((naphthalen-1-yl)methylene)malononitrile (6h) 5 White solid (22 mg, yield 99%), m.p. 164-165. 1 H NMR (4MHz, CD 3 ) δ: 7.62-7.74 (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, 112.54, 113.75, 122.32, 125.41, 127.52, 128.54, 128.6, 129.46, 131.9, 133.55, 134.96, 157.74. MeO 2-(4-methoxybenzylidene)malononitrile (6i) 6 White solid (182 mg, yield 99%), m.p. 11-112. 1 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, 113.41, 114.49, 115.17, 124.4, 133.51, 158.94, 164.87. 2-((E)-3-phenylallylidene)malononitrile (6j) 1 Yellow solid (179 mg, yield 99%), m.p. 126-127. 1 H NMR (4MHz, CD 3 ) δ: 7.27-73.5 (m, 2H), 7.46-7.52 (m, 3H), 7.62-7.66 (m, 3H). 13 C NMR (1MHz, CD 3 ) δ: 82.94, 111.74, 113.59, 122.29, 129.1, 129.39, 132.17, 133.96, 15.55, 16.17. O 2-((furan-2-yl)methylene)malononitrile (6k) 7 Brown solid (143 mg, yield 99%), m.p. 69-7. 1 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: 112.65, 113.86, 114.5, 123.28, 143.12, 148.1, 149.63. S 2-((thiophen-2-yl)methylene)malononitrile (6l) 8 Brown solid (159 mg, yield 99%), m.p. 11-112. 1 H NMR (4MHz, CD 3 ) δ: 7.28 (dd, J 1 = 4. Hz,

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, 113.86, 129.9, 135.42, 137.4, 138.36, 151.24. CO 2 Et O 2 N (E)-ethyl 2-cyano-3-(4-nitrophenyl)acrylate (6n) 9 Yellow solid (244 mg, yield 99%), m.p. 172-173. 1 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, 114.56, 124.34, 131.54, 136.92, 149.71, 151.76, 161.42. CO 2 Et MeO (E)-ethyl 2-cyano-3-(4-methoxyphenyl)acrylate (6o) 9 White solid (224 mg, yield 97%), m.p. 79-8. 1 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, 114.77, 116.25, 124.36, 133.65, 154.4, 163.13, 163.78. CO 2 Et (E)-ethyl 3-(2-chlorophenyl)-2-cyanoacrylate (6p) 3 White solid (233 mg, yield 99%), m.p. 51-52. 1 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), 7.45-7.51 (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, 114.82, 127.48, 129.85, 13.34, 133.71, 136.42, 151.14, 161.8. CO 2 Et (E)-ethyl 3-(3-chlorophenyl)-2-cyanoacrylate (6q) 1 White solid (233 mg, yield 99%), m.p. 1-11. 1 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), 7.9-7.93 (m, 2H), 8.18 (s, 1H). 13 C NMR (1MHz, CD 3 ) δ: 14.15, 63., 14.67, 114.96, 128.65, 13.56, 13.84, 133.7, 135.36, 153.23, 162.1. CO 2 Et (E)-ethyl 3-(4-chlorophenyl)-2-cyanoacrylate (6r) 9 White solid (233 mg, yield 99%), m.p. 91-92. 1 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, 115.29, 129.69, 129.88, 132.22, 139.61, 153.42, 162.25.

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), 1.64-1.82 (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, 115.63, 162.1, 18.7. CO 2 Et Ethyl 2-(4-tert-butylcyclohexylidene)-2-cyanoacetate (8b) 11 Pale solid (232 mg, yield 93%), m.p. 44-45. 1 H NMR (4MHz, CD 3 ) δ:.92 (s, 9H), 1.34 (t, J = 7.2Hz, 3H), 1.42-1.5 (m, 3H), 2.6-2.1 (m, 3H), 2.29-2.38 (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, 115.63, 162.1, 18.16. CO 2 Et Ethyl 2-cyano-2-(4-phenylcyclohexylidene)acetate (8c) 12 Pale solid (24 mg, yield 89%), m.p. 71-72. 1 H NMR (4MHz, CD 3 ) δ: 1.35 (t, J = 7.2Hz, 3H), 1.64-1.81 (m, 2H), 2.19-2.25 (m, 3H), 2.46-2.51 (m, 1H), 2.84-2.92 (m, 1H), 3.18-3.22 (m, 1H), 4.29 (q, J 1 = 7.2Hz, J 2 = 14.4Hz, 2H), 7.18-7.23 (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, 115.55, 126.61, 126.72, 128.62, 144.57, 161.93, 178.3. CO 2 Et NO 2 Ethyl 2-cyano-3-(3-nitrophenyl)but-2-enoate (8d) 13 Yellow solid (169 mg, yield 65%), m.p. 94-95. 1 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, 113.11, 123.24, 127.43, 129.95, 133.81, 138.23, 162.95, 195.72. 2-cyclohexylidenemalononitrile (8e) 7 Colourless liquid (145 mg, yield 99%). 1 H NMR (4MHz, CD 3 ) δ: 1.69-1.87 (m, 6H), 2.64-2.66 (m, 4H). 13 C NMR (1MHz, CD 3 ) δ: 24.99, 27.96, 31.19, 34.75, 82.37, 111.74, 185.31.

Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 References 1 R. Trotzki, M. M. Hoffmann and B. Ondruschka, Green Chem. 28, 1, 767 772. 2 T.-S. Jin, J.-S. Zhang, A.-Q. Wang, T.-S. Li, Synth. Commun. 24, 34, 2611 2616. 3 G. Lai, J. Peng, J. Li, H. Qiu, J. Jiang, K. Jiang, Y. Shen, Tetrahedron Lett. 26, 47, 6951 6953. 4 A. M. Shestopalov, A. P. Yakubov, D. V. Tsyganov, Yu. M. Emel'yanova, V. N. Nesterov, Chem. Heterocycl. Compd. (New York, NY, United States), 22, 38, 118 1189. 5 X. Yang, T. Fox, H. Berke, Org. & Biomol. Chem. 212, 1, 852 86. 6 F. Bigi, M. L. Conforti, R. Maggi, A. Piccinno and G. Sartori, Green Chem. 2, 2, 11 13. 7 M. Feroci, M. Orsini, L. Palombi and A. Inesi, Green Chem. 27, 9, 323 325. 8 J. S. Yadav, B. V. S. Reddy, A. K. Basak, B. Visali, A. V. Narsaiah, K. Nagaiah, Eur. J. Org. Chem. 24, 546 551. 9 G. R. Krishnan, K. Sreekumar, Eur. J. Org. Chem. 28, 4763 4768. 1 S.-X. Wang, J.-T. Li, W.-Z. Yang, Y.-H. Yin, Z.-H. Xie, Synth. Commun. 24, 34, 829 834. 11 A. P. Davis, T. J. Egan, M. G. Orchard, D. Cunningham, P. McArdle, Tetrahedron, 1992, 48, 8725 8738. 12 A. M. Badger, D. A. Schwartz, D. H. Picker, J. W. Dorman, F. C. Bradley, E. N. Cheeseman, M. J. DiMartino, N. Hanna, C. K. Mirabelli. J. Med. Chem. 199, 33, 2963 297. 13 P. M. Titchenell, H. D. Hollis Showalter, Y. Jin, J.-F. Pons, A. J. Barber, D. A. Antonetti, Bioorg. Med. Chem. Lett. 213, 23, 334 338.

41.BC4CDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 Spectra of compounds ( 1 H NMR, 13 C NMR) D3 7.954 7.935 7.819 7.69 7.672 7.653 7.598 7.578 7.56 7.293.3 1 5 1.99 1. 2. 8. 7. 6. 5. 4. 3. 2. 1.. 16.13 3 B134.688 13.954 13.773 129.676 113.75 112.591 76.77 82.877 77.45 77.88 6 5 4 3 2 1 2 15 1 5

41.BCD476.767BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 8.275 8.195 8.175 7.563 7.553 7.487 7.476 7.465 7.455 7.445 7.434 7.265. 7 6 5 4 3 2 1 1. 1.5 2.2-1 1. 5.. 156.96 136.363 135.83 13.733 129.516 129.58 127.818 3 113.248 111.941 85.776 77.43 77.85 1 5 2 15 1 5

41.93BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 7.85 7.835 7.832 7.737 7.617 7.596 7.524 7.53 7.483 7.265 -. 8 7 6 5 4 3 2 1.99.96 1. -1 476.753BCD158.245 135.822 134.389 132.324 13.929 13.463 5. 128.368 113.229 112.55 3 84.69 77.389 77.72. 8 7 6 5 4 3 2 1-1 2 15 1 5

41.99BCD4CDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 7.873 7.851 7.746 7.535 7.514 7.266. 5 1. 2.4 5.. 158.35 3 B141.178 131.88 13.12 129.29 76.756 113.483 112.38 83.34 77.391 77.74 6 5 4 3 2 1 2 15 1 5

41.BCD4CDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3O2N 8.431 8.41 8.122 8.1 7.927 7.293.25 7 6 5 4 3 2 1 2.1 2.1-1 5.. 156.939 15.373 3 B135.826 131.358 124.677 76.746 112.669 111.638 87.541 77.38 77.63 8 7 6 5 O 2 N 4 3 2 1-1 2 15 1 5

43.9BCD4CDCElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 7.826 7.85 7.725 7.352 7.331 7.263 2.461 -. 7 H 3 C 6 5 4 3 2 1 2.2 1. 2.5 5.. l3 159.83 146.439 13.956 13.414 128.48 114.61 112.95 22.6 B81.183 77.48 77.9 76.772 7 6 5 H 3 C 4 3 2 1 2 15 1 5

4.99BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 8.289 7.734 7.727 7.267 7.187 7.179 7.164 7.156 6.944 6.921 3.888 3.816. 6 5 MeO OMe 4 3 2 1 3.13 3.1 1.4 1..98-1 4CD5.. 154.143 153.799 153.47 3 B124.36 12.148 114.386 113.246 112.857 111.179 55.888 8.956 77.399 77.82 76.764 56.355 5 4 MeO OMe 3 2 1 2 15 1 5

476.759BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 1 8.682 3 8.317 8.299 8.155 8.134 8.1 7.978 7.745 7.741 7.727 7.724 7.77 7.73 7.692 7.689 7.671 7.664 7.652 7.644 7.624 7.293.39 5 3.9 2.1 1.1 1. 4.98BCD1. 5.. 157.741 134.967 133.558 3 131.9 129.466 128.65 128.544 127.528 127.332 125.417 122.324 113.757 112.546 85.169 77.394 77.76 5 2 15 1 5

42.BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 7.951 7.929 7.684 7.293 7.54 7.32 3.945.25 6 5 4 MeO 3 2 1 3.6 1. 1.99-1 4CD5.. 3 B164.865 158.941 133.51 124.41 115.173 114.491 113.47 78.516 55.857 5 MeO 2 15 1 5

43.9BElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 CD8 3 7.658 7.655 7.644 7.631 7.624 7.518 7.53 7.483 7.473 7.469 7.462 7.316 7.292.34 7 6 5 4 3 2 1 2.9 2. -1 4CD8. 7. 6. 5. 4. 3. 2. 1.. 16.165 15.549 3 B133.955 132.166 129.387 129.1 122.297 113.586 111.736 76.776 82.947 77.412 77.94 4 3 2 1 2 15 1 5

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42.1BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3CO2Et 8.369 8.347 8.316 8.157 8.135 7.277 4.458 4.44 4.422 4.44 1.445 1.428 1.41. 1 O 2 N 5 3. 2. 1.98.95 4CD14.126 B1. 161.42 151.767 149.714 136.923 131.541 124.34 114.564 3CO2Et 17.373 5. 63.368. 8 7 6 O 2 N 5 4 3 2 1-1 2 15 1 5

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43.17BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3CO2Et 8.688 8.245 8.225 7.519 7.499 7.474 7.458 7.454 7.427 7.49 7.39 7.281 4.437 4.419 4.41 4.383 1.432 1.414 1.396. 7 6 5 4 3 2 1.93 1. 1.5 2.5 2.11-1 4CDC1. l3co2et 14.147 B161.84 151.14 136.425 133.713 13.343 129.852 127.483 114.828 16.164 5. 77.443 77.125 76.86 62.968. 5 2 15 1 5

41.BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3CO2Et 8.187 7.936 7.912 7.97 7.544 7.523 7.478 7.458 7.439 7.269 4.426 4.49 4.391 4.373 1.427 1.49 1.391. 7 6 5 4 3 2 1.99 1.94 1.4 2.11 3.12-1 414.156BCD5.. 3CO2Et 162.15 153.23 135.365 133.79 13.848 13.562 128.65 114.968 14.671 63.4 5 4 3 2 1 2 15 1 5

43.8BCDElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3CO2Et 8.23 7.951 7.929 7.494 7.473 7.27 4.419 4.41 4.384 4.366 1.422 1.44 1.386. 7 6 5 4 3 2 1 2.5 1. 2.1 2.1-1 4CDC5.. l3co2et 14.166 B162.251 153.422 139.61 132.229 129.881 129.698 115.298 13.485 77.376 77.59 76.741 62.9 5 2 15 1 5

Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213

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Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213

Electronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213

43.94BCD424.99BCDCElectronic Supplementary Material (ESI) for RSC Advances This journal is The Royal Society of Chemistry 213 3 2.663 2.654 2.647 1.871 1.88 1.8 1.697 1.69. 5 4 3 2 1 6.3 1. 5.. l3 185.318 111.741 82.378 77.535 77.217 76.899 34.756 31.19 27.966 5 4 3 2 1 2 15 1 5

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