Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2014 Supporting Information For Pyrolysis of azetidinone derivatives: A versatile route toward electron-rich alkenes, C-1 allylation and/or homologation of aldehydes Nouf Al-Hamdan, Osama M. Habib, Yehia A. Ibrahim, Nouria A. Al-Awadi.* Chemistry Department, Faculty of science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. Correspondence author: E-mail address: n.alawadi@ku.edu.kw Tel: (+) 96524985537; Fax: (+) 96524816482 S1 S2 S3 S4 S5 S6 S7 S8 S9 S10 S11 S12 S13 S14 S15 S16 S17 S18 S19 S20 S21 S22 S23 S24 S25 S26 S27 S28 S29 S30 S31 S32 S33 S34 S35 S36 S37 Table 1. Yield, 1H-NMR and 13C-NMR of azetidinones 2a-g, 3d and 4a-g (H-3/C-3 and H-4/C-4) Comp. %yield H3/C3 H4/C4 2a 67%, 5.60 (d, J 4.8)/81.1 5.43 (d, J 4.8)/62.1 2b 60%, 5.60 (d, J 4.8)/81.0 5.40 (d, J 4.8)/61.9 2c 60%, 5.67 (d, J 4.8)/81.2 5.40 (d, J 4.8)/62.2 2d 30% 5.58 (d, J 4.8)/81.4 5.38 (d, J 4.8)/62.2 2e 74% 5.57 (d, J 4.8)/81.2 5.40 (d, J 4.8)/61.9 2f 61% 5.56 (d, J 4.8)/81.2 5.40 (d, J 4.8)/61.7 2g 58% 5.60 (d, J 4.8)/81.0 5.40 (d, J 4.8)/61.1 3d 45% 5.11(d, J 1.8)/87.5 4a 67% 5.93 (d, J 4.8)/79.3 5.38 (d, J 4.8)/70.3 4b 69% 5.89 (d, J 4.4)/79.5 5.35 (d, J 4.4)/70.2 4c 71% 5.87 (d, J 4.4)/79.3 5.35 (d, J 4.4)/70.4 4d 77% 5.90 (d, J 4.8)/79.3 5.38 (d, J 4.8)/70.2 4e 65% 5.89 (d, J 4.4)/79.5 5.35 (d, J 4.4)/70.2 4f 73% 5.87 (d, J 4.4)/79.4 5.34 (d, J 4.4)/69.9 4g 72% 5.88 (d, J 4.8)/79.1 5.35 (d, J 4.8)/69.4 5.00 (d, J 1.8)/64.1 Assignment of H3, H4 proton signals is based on their cross correlations with their respective carbon signals in the 2D-HSQC NMR spectra. S38 S39 S40 S41 S42 S43 S44 S45 S46 S47 S48 S49 S50 S51 S52 S53 S54 S55 S56 S57 S58 S59 S60 S61 S62 S63 S64 S65 S66 S67 S68 S69 S70 S71 Table 2. H-3/C-3 and H-4/C-4 of azetidinone rings of 8a-e, 9a and 10a-e. 8a 75% 4.99 (d, J 4.8)/82.5 5.22 (d, J 4.8)/61.0 8b 84% 4.97 (d, J 4.8)/82.7 5.17 (d, J 4.8)/62.1 8c 69% 4.92 (d, J 4.8)/82.8 5.19 (d, J 4.8)/62.1 8d 82% 4.94 (d, J 4.8)/82.4 5.16 (d, J 4.8)/61.5 8e 70% 4.98 (d, J 4.8)/82.5 5.19 (d, J 4.8)/61.3 9a 4% 4.55 (d, J 2.4) 4.95 (d, J 2.4) 10a 70% 4.72 (d, J 4.4)/80.4 5.75(d, J 4.4)/70.2 10b 75% 4.71 (d, J 4.4)/80.3 5.70(d, J 4.4)/70.3 10c 65% 4.72 (d, J 4.4)/80.6 5.73(d, J 4.4)/70.3 10d 72% 4.68 (d, J 4.4)/80.5 5.70(d, J 4.4)/69.9 10e 68% 4.70 (d, J 4.4)/80.3 5.73(d, J 4.4)/69.5 Assignment of H3, H4 proton signals is based on their cross correlations with their respective carbon signals in the 2D-HSQC NMR spectra. S72 Spectra of some selected product after preparative TLC separation S73 S74 S75 S76 S77 S78