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1 ARKIVC 212 (viii) S1-S Supplementary Material An efficient method for the preparation of 2,2,4- trisubstituted 1,2- dihydroquinolines using catalytic amount Bi(Tf) as catalyst Zeynep Gültekin, a* Wolfgang Frey b a Çankırı Karatekin University, Department of Chemistry, 181, Çankırı, Turkey b University of Stuttgart, Institut für rganische Chemie, Pfaffenwaldring 55, D-7569 Stuttgart, Germany zpgul66@hotmail.com Table of Contents 1. General Methods S1 2. General Procedure for the synthesis of 1,2-dihydroquinolines under room temperature S1. General Procedure for the synthesis of 1,2-dihydroquinolines under microvawe conditions S1 4. Characterization of products a-r and 4, 9 S MR and 1 C MR Spectra of Compounds a-r and 4, 9 S11 General Methods. Acetonitrile, chloroform were distilled from calcium hydride immediately prior to use. DMF, toluene, nitromethane were distilled before use. All aniline derivatives, Bi(Tf), methyl pyruvate are commercially available. Compounds a, 16 n, o, i and c 17 previously reported in the literature. Column chromatography was performed using M silica gel (particle size.4-.6 mm). For thin-layer chromatography (TLC), silica gel coated aluminium plates (Merck, silica gel 6 F 254 ) were used and chromatography was performed using silica gel Merck 6 (particle size.6-.2 mm), visualised by UV irradiation. 1 -MR and 1 C-MR were recorded on a Mercury or 4 spectrometer in CDCl or MeD. Data are reported in the following order: chemical shift ( ) in ppm; multiplicities are indicated bs (broadened singlet), s (singlet), d (doublet), m (multiplet), dd (double doubled); coupling constants (J) are in ertz (z). 1 C MR spectra were acquired on a broad band decoupled mode. Mass spectra was conducted on GC-MS Shimadzu QP21 (column: Equity -5, length I.D. m.25 mm, df.25 μm, lot # 2889-U, Supelco). RMS were measured on a Finnigan MAT 95 or LTQ rbitrap XL spectrometer. IR spectra were measured in a Perkin-Elmer ATR apparatus and are reported in terms of frequency of absorption (cm -1 ). Microwave, CEM marked, Discover SP-D With explorer 12 ybrid was used. General procedure for the synthesis of 1,2-dihydroquinolines under room temperature The -Substituted aniline (1 mg, 1 eq) was dissolved in acetonitrile (1.5 ml) in a screwcapped test tube and Bi(Tf) (5 mol%,.5 eq) and methyl pyruvate (2.2 eq) was added to the mixture. This mixture were stirred at room temperature (For the time see: Table ) until the starting material was completely consumed as monitored by tlc. The resultant residue was direcly purified by flash chromatography on silica (EtAc:Cyclohexane 2:98). All solid products were recrystallized over pentan and ethyl acetate. General procedure for the synthesis of 1,2-dihydroquinolines under microvawe conditions -Substituted aniline (1 mg, 1 eq) was dissolved in acetonitrile (1.5 ml) then Bi(Tf) (5 mol%,.5 eq) and methyl pyruvate (2.2 eq) were added to the solution. This mixture were heated by microwave irradiation (1 bar, 15 watt, 1 o C, See for the time: Table 1,2 and ). Page S1
2 ARKIVC 212 (viii) S1-S The progress of the reaction was monitored through tlc. The resultant residue was direcly purified by flash chromatography on silica (EtAc:Cyclohexane 2:98). All solid products were recrystallized over pentan and ethyl acetate. By this method the following compounds were prepared. Characterization of products a-r and 4, 9 Dimethyl 8-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (a) 16 C C Yellow crystalline solid; yield (71%); R f.5 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 268 (), 1718, 169 (C) cm MR ( Mz, CDCl ): s,, C ), s,, CC ),.76 (s,, CC ),.85 (s,, CC ), (m, 1, Ar- ), (d, 1, J 1.9 z, C=C), (dd, 1, J 8.1 and 1.4 z, Ar- ), (m, 1, Ar- ) 9.6 (bs, 1, ). C-MR (4 Mz, CDCl ): 28.1 (C ), 28.7 (CC ), 52.2, 52.9 (2xCC ), 58.6 (C2), (C8), (C6), (C1), 127. (C7), 11.8 (C5). 12. (C), 12.7 (C4), 146. (C9), (C), (C), 2.4 (C). Anal. Calcd for C : C, 6.6;, 5.65;, Found: C, 6.41;, 5.8;, MS m/z (EI).1 (M +, %), (9), (1), (8), (28), (15), (1), ( 1), 115. (8), 59.2 (4). Dimethyl 6-phenoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (b) C C Yellow solid; yield (77%); R f.4 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 79 (), 1721 (C) cm MR (4 Mz, CDCl ): s,, C ),.76 (s,, CC ),.81 (s,, CC ), 4.49 (br, 1, ), (d, 1, J 8. z, Ar- ), 6.7 (bs, 1, -C=C), (dd, 1, J 8.7 and 2.6 z, Ar- ), (m, 2, Ar- ), (m, 1, Ar- ), (m, 1, Ar- ), 7.61 (bs, 1, Ar-). C-MR (4 Mz, CDCl ): 27.4 (C ), 52.1, 52.8 (2xCC ), 58.7 (C2), (C8), (C7), 117. (C5), (C1), (C6 ) (C2 ), (C4 ), (C and C5 ), 1.7 (C), 18.9 (C4), (C9), 157. (C6), (C1 ), (C), (C). Anal. Calcd for C : C, 67.98;, 5.42;,.96. Found: C, 67.9;, 5.54;,.92; MS m/z (EI) 5.1 (M +, 4%), (19), (1), 25.1 (4), 77.2 (5), 59. (2). Page S2
3 ARKIVC 212 (viii) S1-S Dimethyl 6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (c) 17 C 7 6 C C Yellow oil; yield (58%); R f. (2:1 Cyclohexane/EtAc). IR (kapilar) 68 (), 1726 (C) cm MR (Mz, CDCl ): s,, C ),.72,.74,,85 (s, 9, CMe and 6-Me), 4.4 (bs, 1, ), (d,1, J 8.6z, Ar-), (dd, 1, J 8.6 and 2.8 z, Ar-), 6.74 (bs, 1, -C=C), (d, 1, 2.8 z, Ar-). C-MR ( Mz, CDCl ): 26.9 (C ), 52., 52.7 (CC ), 55.7 (C ), 58.5 (C2), (C8), (C5), (C1), (C7), (C), 14.2 (C4), 16.6 (C9), (C6), 166. (C), (C). Anal. Calcd for C : C, 61.85;, 5.88;, Found: C, 61.62;, 6.1;, 5.6. MS m/z (EI) (M +, 11%), 2. (26), 22.2 (1), 17.2 (7), 11.2 (6), (4). Dimethyl 6,7-dimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (d) C C C 2 C Yellow oil; yield (62%); R f.16 (2:1 Cyclohexane/EtAc). IR (kapilar) 67 (), 1725 (C) cm MR ( Mz, CDCl ): s,, C ),.72,.8,,82,.8 (s, 12, CC and 6,7-C ), 4.6 (bs, 1, ), 6.21 (s,1, Ar-), 6.57 (s, 1, Ar-), 7.54 (s, 1, -C=C). C-MR ( Mz, CDCl ): 26.9 (C ), 51.9, 52.6 (CC ), 55.6, 56.4 (C ), 58.5 (C2), 98.4 (C8), 18.6 (C5), 11.5 (C9), (C), 1.6 (C4), 17.7 (C6), (C1), 15.5 (C7), (C), (C). Anal. Calcd for C : C, 59.81;, 5.96;, 4.6. Found: C, 55.65;, 5.81;,.918. MS m/z (EI) 21.2 (M +, 14%), 26.2 (25), (1), (16), (7), 2.2 (5), 11.1 (6). Dimethyl 5,8-dimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (e) C C 1 C 2 C Yellow solid; yield (45%); R f.2 (2:1 Cyclohexane/EtAc); m.p: 1-11 o C. IR (KBr) 81 (), 1727 (C) cm MR ( Mz, CDCl ): s,, C ),.7,.71,,78, Page S
4 ARKIVC 212 (viii) S1-S.81 (s, 12, CC and 5,8-C ), 4.9 (bs, 1, ), 6. (s, 1, -C=C), (d,1, J 8.8 z, Ar-), (d, 1, J 8.8 z, Ar-). C-MR (4 Mz, CDCl ): 26.8 (C ), 52., 52.6 (CC ), 56.1, 56.2 (C ), 57.6 (C2), 99.6 (C1), 17.6 (C6), (C7), (C8), (C), 14. (C4), (C9), (C5), (C), (C). Anal. Calcd for C : C, 59.81;, 5.96;, 4.6. Found: C, 59.;, 5.61;, MS m/z (EI) 21.1 (M +, 5%), 26.1 (16), (1), (6), 22.1 (), 22.1 (4), 17.1 (). Dimethyl 6- t Butyl -2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (f) 6 7 C C 1 Yellow solid; yield (7%); R f.66 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 6 (), 174, 1718 (C) cm MR (4Mz, CDCl ): s, 9, t Bu s,, C ),.7 (s,, CC ),.86 (s,, CC ), 4.4 (bs, 1, ), (d, 1, J 8., Ar- ), 6.65 (bs, 1, -C=C), (d, 1, J 8., Ar- ), 7.86 (br, 1, Ar- ). C- MR (4Mz, CDCl ): 27.6 (C ), 1., 1.2, 1. (-C(C ) ), 1.5 (-C(C ) ), 52., 52.7 (2xCC ), 58.5 (C2), 11.6 (C8), 12.4 (C1), 12.2 (C5), (C7), 128. (C) (C4), 14. (C6), (C9), (C), (C). Anal. Calcd for C : C, 68.12;, 7.;, Found: C, 67.7;, 7.44;, 4.. MS m/z (EI) 17.2 (M +, 4%), (18%), (1), 24.2 (1), (15), (6), (). Dimethyl 6-methoxy-2,8-dimethyl-1,2-dihydroquinoline-2,4-dicarboxylate (g) C 5 4 C C Yellow solid; yield (77%); R f.5 (2:1 Cyclohexane/EtAc); m.p: 82-8 o C. IR (KBr) 82 (), 174, 1718 (C) cm MR (4Mz, CDCl ): s,, C ), 2.2 (s,, C ),.7 (s,, CC ),.7 (s,, C ),.84 (s,, CC ), (d, 1, J 2.6, Ar- ), 6.7 (br, 1, -C=C), (d, 1, J 2.6, Ar-). C-MR (4 Mz, CDCl ): C 27.2 (C ), 52., 52.8 (CC ), 55.7 (C ), 58.5 (C2), 19.(C5), 117. (C1), (C7), (C8), 128. (C). 1.6 (C4), 14.8 (C9), (C6), 166. (C), (C). Anal. Calcd for C : C, 62.94;, 6.27;, Found: C, 62.84;, 6.42;, MS m/z (EI) 5.1 (M +, 6%), (2), (1), 2.1 (8), (7), (4). Page S4
5 ARKIVC 212 (viii) S1-S Dimethyl 6- phenyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (h) C C Yellow solid; yield (65%); R f.56 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 64 (), 1712 (C) cm MR ( Mz, CDCl ): s,, C ),.76 (s,, CC ),.88 (s,, CC ), 4.58 (bs, 1, ), (bs, 2, -C=C and Ar-), (m, 1, Ar-), (m,, Ar- ), (m, 2, Ar- ), 8.1 (br, 1, Ar- ). C-MR (4 Mz, CDCl ): 27.7 (C ), 52.1, 52.9 (2xCC ), 58.7 (C2), (C8), (C1), (C2 ), (C7), (C6 ) (C4 ), 127. (C5), (C), 128. (C5 ), (C ), 11.5 (C6), 12.9 (C4), 141. (C1 ), (C9), (C), (C). Anal. Calcd for C : C, 71.2;, 5.68;, Found: C, 7.99;, 5.77;, MS m/z (EI) 7.2 (M +, 7%), (21), (1), (7), 19.2 (4), 59. (2). Compound (i) 17b C C Yellow solid; yield (5%); R f.56 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 96 (), 172 (C) cm MR ( Mz, CDCl ): s,, C ),.77 (s,, CC ),.89 (s,, CC ), 5. (bs, 1, ); (d, 1, J 8.5 z, Ar-), 6.68 (s, 1, C=C), (d, 1, J 8.7 z, Ar-), (m, 2, Ar-), (m, 1, Ar- ), (m, 1, Ar-), (d, 1, J 8.7 z, Ar-). C-MR ( Mz, CDCl ): 27. (C ), 52., 52.9 (2xCC ), 58.6 (C2), (C1), (C6), (C5), (C12), 12.9 (C9) (C8), (C7), (C), 129. (C), 1.2 (C11), 14.2 (C4), 17.9 (C14), (C), (C). Anal. Calcd for C : C, 69.44;, 5.5;, 4.5. Found: C, 69.4;, 5.55;, MS m/z (EI) 11.1 (M +, 16%), 25.2 (5), (1), (21), 59. (2). Compound (j) Page S5
6 ARKIVC 212 (viii) S1-S Yellow solid; yield (67%); R f.4 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 51 (), 1716 (C) cm MR (4 Mz, CDCl ): s,, C ),.7 (s,, CC ),.8 (s,, CC ), 6.44 (s, 1, -C=C), (d, 1, J 8.7 z, Ar-), (m, 1, Ar-), (m, 2, Ar-), (m, 2, Ar-). C-MR (4Mz, CDCl ): 25.5 (C ), 52., 52.8 (2xCC ), 57.8 (C2), 11.4 (C1), 117. (C7), (C5), 12.4 (C9), (C8) (C12), (C1), (C6), (C), 1. (C14), 1.9 (C4), 142. (C11), (C), 174. (C). Anal. Calcd for C : C, 69.44;, 5.5;, 4.5. Found: C, 69.52;, 5.7;, 4.45; MS m/z (EI) 11.1 (M +, 5%), 25.1 (19), (1), 19.1 (1), (4), 59. (). Dimethyl 2,6,8-trimethyl -1,2-dihydroquinoline-2,4-dicarboxylate (k) C C Pale yellow crystalline solid; yield (6%); R f.25 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 52 (), 174, 179 (C) cm MR (4 Mz, CDCl ): s,, C ), 2.1, 2.2 (s, 6, 2xC ),.7,.8 (s, 6, 2xCC ), 6. (s, 1, Ar-), 6.42 (bs, 2, Ar- and -C=C). C-MR (4 Mz, CDCl ): XC 26.9 (C ), 52.2, 52.7 (CC ), 57.7, (C2), 11.5(C1), 12. (C8), 1.4, 1.9 (C5 and C6), 14.7 (C7), 19.4 (C4), 14.4 (C9), 169. (C), 174. (C). Anal. Calcd for C : C, 66.42;, 6.62;, Found: C, 66.41;, 6.69;, MS m/z (EI) (M +, 5%), 21.2 (28), 2.1 (1), (8), (15), 17.1 (9), (6). Dimethyl 6- acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (I) 6 7 C C 1 Yellow crystalline solid; yield (91%); R f.1 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 29 (), 1742, 1664 (C) cm MR (4 Mz, CDCl ): s,, C ), s,, CC ),.74 (s,, CC ),.86 (s,, CC ), 5. (br, 1, ); (d, 1, J 8.5 z, Ar- ), 6.69 (br, 1, C=C), (dd, 1, J 8.5 and 2. z, Ar- ), (d, 1, J 2. z, Ar- ). C-MR (4 Mz, CDCl ): 26.1 (C ), 28.2 (CC ), 52.2, 5. (2xCC ), 58.9 (C2), 11.5 (C8), (C1), 127. (C6), (C5), (C). 1. (C7), 12.4 (C4), (C9), (C), 17. (C), 196. (C). Anal. Calcd for Page S6
7 ARKIVC 212 (viii) S1-S C : C, 6.6;, 5.65;, Found: C, 6.42;, 5.7;, 4.6. MS m/z (EI).2 (M +, %), (14), (1), 21.2 (7), (4), (), 59.4 (1). Dimethyl 6- cyano-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (m) C C C White solid; yield (71%); R f.2 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 51 (), 1724, 1718 (C) cm MR (4Mz, CDCl ): s,, C ),.78 (s,, CC ),.87 (s,, CC ), 4.9 (br, 1, ), (d, 1, J 8. z, Ar- ), 6.75 (br, 1, -C=C), (dd, 1, J 8. and 1.8 z, Ar- ), (d, 1, J 1.8, Ar- ). C-MR (4 Mz, CDCl ): 28.4 (C ), 52.4, 5.2 (2xCC ), 58.9 (C2), 1.7 (C6), 114. (C8), (C1), (C), (C7). 11. (C), 1.4 (C4), 1.5 (C5), (C9), 165. (C), 17.1 (C). Anal. Calcd for C : C, 62.9;, 4.9;, Found: C, 62.96;, 4.82;, MS m/z (EI) 86.1 (M +, 1%), (15%), (1), (5), 168. (2), (6), 14.1 (6), 59.2 ( 4). Dimethyl 6-nitro-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (n) 17 C C Yellow solid; yield (97%); R f.2 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 47 (), 1721 (C) cm MR (Mz, CDCl ): s,, C ),.8 (s,, CC ),.9 (s,, CC ), 5.22 (bs, 1, ), (d, 1, J 8.9 z, Ar-), 6.78 (d, 1, J 1.54 z, C=C), (dd, 1, J 8.9 and 2.5 z, Ar-), (d, 1, J 2.5, Ar-). C-MR (4 Mz, CDCl ): 28.6 (C ), 52.5, 5. (2xCC ), 59. (C2), 11. (C8), (C1), 12.4 (C5), (C7), (C). 1. (C4), 19.1 (C6), (C9), (C), (C). Anal. Calcd for C : C, 54.9;, 4.61;, Found: C, 54.84;, 4.45;, MS m/z (EI) 6.1 (M +, 1%), (15), (1), 21.1 (47), (12), (9), 59. ( 5). Page S7
8 ARKIVC 212 (viii) S1-S Dimethyl 2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (o) C C Yellow solid; yield (6%); R f.5 (2:1 Cyclohexane/EtAc); m.p: 7 o C. IR (KBr) 65 (), 171 (C) cm MR (4 Mz, CDCl ): s,, C ),.7 (s,, CMe),.8 (s,, CMe), 4.5 (bs, 1, ), (m,1, Ar-), 6.66 (s, 1, -C=C), (m, 1, Ar-), (m, 1, Ar-), (m, 1, Ar-). C-MR (4 Mz, CDCl ): 27.6 (C ), 52., 52.8 (CC ), 58.5 (C2), (C5), 116. (C8), (C6), (C1), (C7), (C), 12.5 (C4), (C9), 166. (C), (C). Anal. Calcd for C : C, 64.6;, 5.79;, 5.6. Found: C, 64.4;, 5.81;, MS m/z (EI) (M +, %), 2.1 (15), 22.1 (1), (4), (5), 14.1 (18), (7), (7), 59.1(5). Dimethyl 5,6,7-trimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (p) C Me 6 5 Me C Me 8 1 White crystalline solid; yield (8%); R f.16 (2:1 Cyclohexane/EtAc); m.p: o C. IR (KBr) 59 (), 179 (C) cm MR ( Mz, CDCl ): s,, C ),.69,.71,,79,.8 (s, 15, CC and 5,6,7-C ), 4.42 (bs, 1, ), 5.85 (bs, 1, Ar- ), 5.99 (s, 1, -C=C). C-MR ( Mz, CDCl ): 26.9 (C ), 52.1, 52.6 (CC ), 55.7, 58. (2xC ), 58.(C2), 6.9 (C ), 9.7 (C8), 14. (C1), 12.8 (C), 129. (C4), 14.2 (C9), 19.7 (C5), (C6), (C7), 17. (C), (C). Anal. Calcd for C : C, 58.11;, 6.2;,.99. Found: C, 57.7;, 5.91;,.9. MS m/z (EI) 51.2 (M +, 7%), 29.1 (19), (1), (6), (7), 1.1 (). Dimethyl 6-bromo-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (q) Br C C Yellow crystalline solid; yield (81%); R f.5 (2:1 Cyclohexane/EtAc); m.p: o C. Page S8
9 ARKIVC 212 (viii) S1-S IR (KBr) 52 (), 1724 (C) cm MR (4Mz, CDCl ): s,, C ),.74 (s,, CC ),.85 (s,, CC ), 4.51 (bs, 1, ), (d, 1, J 8.5 z, Ar-), 6.71 (bs, 1, -C=C), (dd, 1, J 8.5 and 2.1 z, Ar- ), (d, 1, J 2.1, Ar- ). C-MR (4 Mz, CDCl ): 27.5 (C ), 52.4, 52.9 (2xCC ), 58.6 (C2), 11.4 (C6), (C8), (C9), 127. (C7), 129. (C) (C5), 1.8 (C4), (C9), (C), 17.9 (C). Anal. Calcd for C Br 4 : C, 49.4;, 4.15;, Found: C, 49.8;, 4.1;, 4.1. MS m/z (EI) 9. (M +, 5%), 28. (12%), 282. (97), 28. (1%), 221. (7), 21.1 (11), (6), ( 6), 59.2 (6). Dimethyl 6-iodo-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate (r) C I C Yellow crystalline solid; yield (4%); R f.56 (2:1 Cyclohexane/EtAc); m.p: 12 o C. IR (KBr) 5 (), 172 (C) cm MR (4 Mz, CDCl ): s,, C ),.74 (s,, CC ),.86 (s,, CC ), 4.51 (bs, 1, ), (d, 1, J 8.4 z, Ar- ), (d, 1, J 2. z, -C=C), (dd, 1, J 8.4 and 2. z, Ar- ), (d, 1, J 2., Ar-). C-MR (4 Mz, CDCl ): 27.6 (C ), 52.24, (2xCC ), 58.5 (C2), (C8), (C1), (C), 1.5 (C4), 14.8 (C5). 18. (C7), 142. (C9), (C), 17.9 (C). Anal. Calcd for C I 4 : C, 4.4;,.64;,.62. Found: C, 4.81;,.58;,.56. MS m/z (EI) 87.1 (M +, 7%), 29. (11), 28. (1), 21.2 (2), (4), 59. (2). Dimethyl 6-acetyl-4-hydroxy-2-methyl-1,2,,4-tetrahydroquinoline-2,4-dicarboxylate (4) White solid; yield (54%); R f.5 (1:1 Cyclohexane/EtAc); m.p: 2-21 o C. IR (KBr) 25 (), 174 (C) cm MR (Mz, MeD): s,, C ), (AB, 2, J AB 1.7 z, -C 2 ), 2.4 (s,, CC ),.6 (s,, CC ),.77 (s,, CC ), (d, 1, J 8.4 z, Ar- ), (d, 1, J 2. z, Ar- ), (dd, 1, J 8.6 and 2. z, Ar- ). MS m/z (EI) 21.2 (M +, 21%), 26.2 (5), (28), (2), (1), 22.2 (29) (7), 1.2 (4), 59.2 (4). RMS-EI calcd. for C [M+]: ; Found: Page S9
10 ARKIVC 212 (viii) S1-S Lactone (9) MW (1 bar, 15 watt, 1 o C, 7 h). Pale purple solid; yield (2%); R f.4 (1:1 Cyclohexane/EtAc); m.p: o C. 1 -MR (Mz, CDCl ): s,, C ),.8 (s,, Me), 6.4 (s, 1, =C), 6.94 (1, br, ), (1, dd, J 5. and 8., Ar-), (1, dd, J 1. and 8. z, Ar-), (1, dd, J 1.4 and 4.6 z, Ar-). C- MR (4 Mz, CDCl ): 2.1 (C ), 5.4 (C ), (C2), (C), (C5 ), 12.2 (C4 ), 128. (C6 ), 1.9 (C2 ), 19.9 (C ), 141,6 (C4), (C), (C). Crystal data for 9: C Cl 2 4, M = , crystallizes as colourless blocks, crystal dimensions.5 x. x.2 mm. Monoclinic, a = 7.575(1) Å, b = 14.47(2) Å, c = (14) Å, β = (1), V = 126.9() Å, z = 4, D c = Mgm -, space group P2 1 /c (o. 14), MoK α radiation (λ =.717), μ =.14 mm -1, F() = 584. The X-ray data were collected at 29(2) K in the range 4.5 < 2θ < 56 on a icolet P/F diffractometer by the Wyckoff scan method. The 44 unique reflections were corrected for Lorentzian polarization effects, but not for absorption. Intensity of 1647 reflections were larger than 2σ(I). The structure was solved by Direct Methods and refined by full matrix least squares methods of F 2 with SELXTL-97 program package. ydrogen atoms were included in calculated positions and refined in riding mode. Refinement converged at a final R =.85 (wr 2 =.1548, I>2σ(I), 179 parameters, mean and maximum δ/σ. and.), with allowance of anisotropic displacement parameters for all non-hydrogen atoms. Minimum and maximum final rest-electron density is.255 and.26 eå -. Page S1
11 ARKIVC 212 (viii) S1-S 1 MR and 1 C MR Spectra of Compounds a-r and 4, Figure S1. MR Spectrum of compound a. Page S11
12 ARKIVC 212 (viii) S1-S Ph Figure S2. MR Spectrum of compound b. Page S12
13 ARKIVC 212 (viii) S1-S Me Figure S. MR Spectrum of compound c. Page S1
14 ARKIVC 212 (viii) S1-S Figure S4. MR Spectrum of compound d. 5 Page S14
15 ARKIVC 212 (viii) S1-S Figure S5. MR Spectrum of compound e. 5 Page S15
16 ARKIVC 212 (viii) S1-S C C C ppm (f1) Figure S6. MR Spectrum of compound f. 5 Page S16
17 ARKIVC 212 (viii) S1-S C C C C C ppm (f1) Figure S7. MR Spectrum of compound g. 5 Page S17
18 ARKIVC 212 (viii) S1-S Figure S8. MR Spectrum of compound h. Page S18
19 ARKIVC 212 (viii) S1-S C C C C C C Figure S9. MR Spectrum of compound i. 5 Page S19
20 ARKIVC 212 (viii) S1-S Figure S1. MR Spectrum of compound j. Page S2
21 ARKIVC 212 (viii) S1-S ppm (f1) Figure S11. MR Spectrum of compound k. Page S21
22 ARKIVC 212 (viii) S1-S Figure S12. MR Spectrum of compound l. Page S22
23 ARKIVC 212 (viii) S1-S 7 C C C C C Figure S1. MR Spectrum of compound m. Page S2
24 ARKIVC 212 (viii) S1-S ppm (f1) Figure S14. MR Spectrum of compound n. 5 Page S24
25 ARKIVC 212 (viii) S1-S C C C C C C Figure S15. MR Spectrum of compound o. 5 Page S25
26 ARKIVC 212 (viii) S1-S Figure S16. MR Spectrum of compound p. Page S26
27 ARKIVC 212 (viii) S1-S Br Br Figure S17. MR Spectrum of compound q. 5 Page S27
28 ARKIVC 212 (viii) S1-S I C C C I Figure S18. MR Spectrum of compound r. 5 Page S28
29 ARKIVC 212 (viii) S1-S ppm (f1) Figure S19. MR Spectrum of compound 4. Page S29
30 General Papers ARKIVC 212 (viii) S1-S C C Cl ppm C C Cl ppm Figure S2. MR Spectrum of compound 9. Page S
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