Supporting Information
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- Λευί Περσεύς Βενιζέλος
- 7 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State Key Laboratory of rganometallic Chemistry, Shanghai Institute of rganic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai China. 1
2 General Remarks. 1 and 13 C NMR spectra were recorded on a Bruker AM-300 spectrometer for solution in CDCl 3 with tetramethylsilane (TMS) as an internal standard; J-values are in z. Mass spectra were recorded by ESI and MALDI methods, and RMS was measured on a Finnigan MA + mass spectrometer. CN microanalyses were recorded on a Carlo-Erba 1106 analyzer. TF and toluene were distilled from sodium (Na) under argon (Ar) atmosphere. C 3 CN and 1,2-dichloroethane were distilled from Ca 2 under argon (Ar) atmosphere. Commercially obtained reagents were used without further purification. All reactions were monitored by TLC with uanghai GF 254 silica gel coated plates. Flash column chromatography was carried out using mesh silica gel at increased pressure. General procedure for the Lewis acid-catalyzed reaction of MCPs with diphenylphosphine oxide in the presence of sulfur or selenium. Under an argon atmosphere, to a solution of 1,1-diphenylmethylenecyclopropane 1a (62 mg, 0.3 mmol) in DCE (2.0 ml) was added diphenylphosphine oxide (91 mg, 0.45 mmol), sulfur (14 mg, 0.45 mmol) or selenium powder (34 mg, 0.45 mmol) and Sn(Tf) 2 (12 mg, 0.03 mmol). The reaction mixture was stirred at 85 o C for 1 h (monitored by TLC). Then the solvent was removed under reduced pressure and the residue was purified by a flash column chromatography (Si 2 ) to give the corresponding products 2a (113 mg, 86%) as a white solid. 2
3 2a Diphenylphosphinothioic acid S-(4,4-diphenylbut-3-enyl) ester (2a). A white solid, m.p o C; IR (C 2 Cl 2 ): ν 3075, 3023, 1655, 1596, 1494, 1438, 1200, 1115, 926, 753, 724, 698, 568 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.43 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.89 (2, dt, J = 7.2, 10.2 z, C 2 ), 6.01 (1, t, J = 7.2 z, =C), (16, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 29.1 (d, J C-P = 2.3 z), 30.4 (d, J C-P = 5.2 z), 126.1, 127.0, 127.2, 128.0, 128.4, 128.6, 129.6, 131.4, 132.2, 132.4, 133.8, 139.4, 142.0, 143.7; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.50; MS (ESI) m/z (%): 441 (47) [M + +1]; RMS (MALDI) Calcd. for C PS +1 (M + +1) requires , Found:
4 2b Diphenylphosphinothioic acid S-(4,4-di-p-tolyl-but-3-enyl) ester (2b). A yellow oil; IR (C 2 Cl 2 ): ν 3022, 2920, 1510, 1437, 1200, 1114, 1097, 820, 698, 751, 723, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.04 (3, s, C 3 ), 2.31 (3, s, C 3 ), 2.43 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.88 (2, dt, J = 7.2, 9.6 z, C 2 ), 5.93 (1, t, J = 7.2 z, =C), (8, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 21.0, 21.2, 29.2 (d, J C-P = 2.3 z), 30.5 (d, J C-P = 5.2 z), 125.1, 127.2, 128.2, 128.6, 128.8, 129.6, 131.4, 132.2, 132.5, 134.0, 136.6, 136.8, 139.6, 143.5; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.47; MS (ESI) m/z (%): 485 (100.00) [M + +17]; RMS (MALDI) Calcd. for C PNaS +1 (M + +Na) requires , Found:
5 Cl Cl 2c Diphenylphosphinothioic acid S-[4,4-bis(4-chlorophenyl)but-3-enyl] ester (2c). A colorless oil; IR (C 2 Cl 2 ): ν 3057, 2920, 1713, 1661, 1589, 1491, 1437, 1400, 1198, 1115, 1092, 1071, 1027, 998, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.42 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.90 (2, dt, J = 7.2, 9.9 z,c 2 ), 6.0 (1, t, J = 7.2 z, =C), 7.01 (2, d, J = 7.8 z, Ar), 7.08 (2, d, J = 7.8 z, Ar), 7.22 (2, d, J = 8.7 z, Ar), 7.32 (2, d, J = 8.7 z, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 28.9 (d, J C-P = 2.3 z), 30.7 (d, J C-P = 5.2 z), 127.3, 128.3, 128.5, 128.6, 131.0, 131.4, 132.3, 132.4, 133.2, 133.3, 133.8, 137.4, 140.1, 141.5; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.40; MS (ESI) m/z (%): 509 (15) [M + +1]; RMS (MALDI) Calcd. for C Cl 2 PS +1 (M + +1) requires , Found:
6 Me Me 2d Diphenylphosphinothioic acid S-[4,4-bis(4-methoxyphenyl)but-3-enyl] ester (2d). A colorless oil; IR (C 2 Cl 2 ): ν 3056, 3002, 2953, 1712, 1646, 1605, 1574, 1509, 1438, 1287, 1178, 1114, 1097, 1032, 822, 568 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.43 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.88 (2, dt, J = 7.2, 9.6 z, C 2 ), 3.76 (3, s, C 3 ), 3.81 (3, s, C 3 ), 5.86 (1, t, J = 7.2 z, =C), 6.78 (2, d, J = 8.7 z, Ar), 6.87 (2, d, J = 8.7 z, Ar), 7.01 (2, d, J = 9.0 z, Ar), 7.11 (2, d, J = 9.0 z, Ar), (6, m, Ar), (6, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 29.2 (d, J C-P = 1.8 z), 30.5 (d, J C-P = 5.4 z), 55.0, 55.1, 113.3, 124.0, 128.3, 128.6, 130.7, 131.4, 131.9, 132.1,, 132.4, 133.8, 135.1, 142.7, 158.5, 158.8; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.57; MS (EI) m/z (%): 501 (2.63) [M + ], 387 (2.03), 268 (6.04), 267 (38.37), 266 (100), 265 (2.26); RMS (MALDI) Calcd. for C PS +1 (M + ) requires , Found:
7 Cl 2e (E-, Z-) Diphenylphosphinothioic acid S-[4-(4-chlorophenyl)-4-phenylbut-3-enyl] ester (2e) (E/Z = 1:1). A colorless oil; IR (C 2 Cl 2 ): ν 3056, 1660, 1589, 1489, 1438, 1199, 1115, 1093, 1070, 1027, 1014, 998, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ (2, m, C 2 ), (2, m, C 2 ), (1, m, =C), (14, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 28.9 (d, J C-P = 2.3 z), 29.0 (d, J C-P = 2.3 z), 30.4 (d, J C-P = 5.2 z), 30.6 (d, J C-P = 5.1 z), 126.6, 127.1, , , , , 128.3, , , 128.5, 128.7, 129.6, 131.0, 131.3, 131.4, 132.2, 132.3, 132.4, 132.9, 133.0, 133.8, 137.8, 139.0, 140.5, 140.6, 141.5, 142.6, 142.7; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.54, 44.47; MS (ESI) m/z (%): 475 (100) [M + +1]; RMS (MALDI) Calcd. for C ClPS +1 (M + +1) requires , Found:
8 F F 2f Diphenylphosphinothioic acid S-[4,4-bis(4-fluorophenyl)but-3-enyl] ester (2f). A colorless oil; IR (C 2 Cl 2 ): ν 3057, 1660, 1601, 1507, 1438, 1224, 1198, 1115, 1071, 1015, 838, 698, 569 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.42 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.89 (2, dt, J = 7.2, 10.5 z, C 2 ), 5.94 (1, t, J = 7.2 z, =C), (8, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 29.0 (d, J C-P = 2.3 z), 30.5 (d, J C-P = 4.6 z), 114.8, 115.0, 115.1, 115.4, (d, J C-F = 1.2 z), 128.5, (d, J C-F = 2.9 z), 128.8, (d, J C-F = 1.2 z), 131.4, (d, J C-F = 4.2 z), 132.4, 133.8, (d, J C-F = 3.5 z), (d, J C-F = 4.0 z), 141.7, (d, J C-F = z), (d, J C-F = z); 31 P NMR ( Mz, CDCl 3, TMS): δ 44.56; MS (ESI) m/z (%): 477 (100) [M + +1]; RMS (MALDI) Calcd. for C F 2 PS +1 (M + +1) requires , Found:
9 Me 2g (E-, Z-) Diphenylphosphinothioic acid S-[4-(4-methoxyphenyl)-4-phenylbut-3-enyl] ester (2g) (E/Z = 1:1). A colorless oil; IR (C 2 Cl 2 ): ν 3055, 2927, 1606, 1574, 1510, 1493, 1298, 1199, 1114, 1070, 1032, 832, 698, 568 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ (4, m, C 2 ), (4, m, C 2 ), 3.76 (3, s, C 3 ), 3.82 (3, s, C 3 ), 5.93 (1, m, =C), (30, m, Ar), (8, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 29.1 (d, J C-P = 2.5 z), 29.2 (d, J C-P = 2.6 z), 30.4 (d, J C-P = 6.0 z), 30.6 (d, J C-P = 5.2 z), 55.1, 55.2, 113.4, 113.5, 124.3, 125.8, 127.0, 127.1, 127.3, 128.0, 128.1, 128.3, 128.5, 128.6, 129.6, 130.8, 131.3, 131.4, 131.7, 132.1, 132.2, 132.4, 133.8, 134.7, 139.7, 142.5, 143.1, 143.3, 158.5, 158.8; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.54, 44.57; MS (ESI) m/z (%): 487 (100) [M + +17], 471 (10) [M + +1]; RMS (MALDI) Calcd. for C PSNa +1 (M + +Na) requires , Found:
10 2h (E-, Z-) Diphenylphosphinothioic acid S-(4-phenylpent-3-enyl) ester (2h) (E/Z = 4:1). A yellow oil; IR (C 2 Cl 2 ): ν 3055, 2922, 1714, 1493, 1438, 1200, 1114, 1070, 1027, 997, 698, 567 cm -1 ; E-isomer: 1 NMR (300 Mz, CDCl 3, TMS): δ 1.95 (3, s, C 3 ), 2.53 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.90 (2, dt, J = 7.2, 10.8 z, C 2 ), 5.67 (1, t, J = 7.2 z, =C), (16, m, Ar), (4, m, Ar); Z-isomer: 1 NMR (300 Mz, CDCl 3, TMS): δ 1.99 (3, s, C 3 ), 2.29 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.78 (2, dt, J = 7.2, 10.8 z, C 2 ), 5.33 (1, t, J = 7.2 z, =C), (16, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 15.9, 16.0, 28.9 (d, J C-P = 2.1 z), 29.0 (d, J C-P = 2.2 z), 29.8 (d, J C-P = 5.2 z), 29.9 (d, J C-P = 5.2 z), 124.9, 125.6, 126.6, 127.7, 128.1, 128.2, 128.4, 128.5, 128.6, 128.7, 129.1, , , 131.4, 131.5, 131.7, 132.2, 132.3, 137.2, 143.3; 31 P NMR ( Mz, CDCl 3, TMS): δ 45.20, 45.29; MS (ESI) m/z (%): 379 (100) [M + +1]; RMS (MALDI) Calcd. for C PS +1 (M + ) requires , Found:
11 2i (E-) Diphenylphosphinothioic acid S-(4-phenylbut-3-enyl) ester (2i). A white solid, m.p o C; IR (C 2 Cl 2 ): ν 3056, 3025, 2927, 1589, 1492, 1481, 1437, 1309, 1199, 1114, 1070, 1027, 966, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.53 (2, dt, J = 7.5, 7.5 z, C 2 ), 2.94 (2, dt, J = 7.5, 10.2 z, C 2 ), 6.10 (1, dt, J = 7.5, 15.9 z, =C), 6.37 (1, d, J = 15.9 z, =C), (5, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 28.8 (d, J C-P = 2.3 z), 33.9 (d, J C-P = 4.6 z), 126.1, 127.2, 128.4, 128.7, 131.3, 131.5, 132.1, 132.5, 134.0, 137.0; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.48; MS (ESI) m/z (%): 365 (100) [M + +1]; Anal. Calcd. for C PS requires C, 72.50;, 5.81%. Found: C, 72.57;, 5.95%. 11
12 2j (E-) Diphenylphosphinothioic acid S-(4-o-tolyl-but-3-enyl) ester (2j). A yellow oil; IR (C 2 Cl 2 ): ν 3056, 3022, 2928, 1438, 1460, 1437, 1200, 1114, 1070, 1027, 967, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.30 (3, s, C 3 ), 2.56 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.95 (2, dt, J = 7.2, 10.2 z, C 2 ), 5.97 (1, dt, J = 7.2, 15.3 z, =C), 6.58 (1, d, J = 15.3 z, =C), (3, m, Ar), (7, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 19.8, 28.9 (d, J C-P = 2.3 z), 34.1 (d, J C-P = 5.1 z), 125.5, 125.9, 127.2, 128.4, 128.5, 130.0, 131.3, 131.5, 132.5, 133.9, 135.0, 136.2; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.50; MS (ESI) m/z (%): 379 (100) [M + +1]; RMS (MALDI) Calcd. for C PS +1 (M + +1) requires , Found:
13 2k (E-) Diphenylphosphinothioic acid S-(4-p-tolyl-but-3-enyl) ester (2k). A yellow oil; IR (C 2 Cl 2 ): ν 3023, 2920, 1512, 1437, 1309, 1200, 1114, 1098, 1070, 1027, 968, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.30 (3, s, C 3 ), 2.50 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.93 (2, dt, J =7.2, 10.2 z, C 2 ), 6.04 (1, dt, J = 7.2, 15.9 z, =C), 6.33 (1, d, J = 15.9 z, =C), (4, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 21.05, 28.8 (d, J C-P = 2.3 z), 33.9 (d, J C-P = 5.2 z), 125.9, 128.5, 129.1, 131.3, 131.9, 132.2, 132.5, 133.9, 134.2, 136.9; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.50; MS (ESI) m/z (%): 379 (100) [M + +1]; RMS (MALDI) Calcd. for C PS +1 (M + +1) requires , Found:
14 2l (E-) Diphenylphosphinothioic acid S-(4-m-tolyl-but-3-enyl) ester (2l). A yellow oil; IR (C 2 Cl 2 ): ν 3023, 2920, 1603, 1482, 1437, 1200, 1114, 1098, 1070, 965, 698, 567 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.32 (3, s, C 3 ), 2.52 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.93 (2, dt, J = 7.2, 10.2 z, C 2 ), 6.08 (1, dt, J = 7.2, 12.0 z, =C), 6.34 (1, d, J = 12.0 z, =C), (4, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 21.05, 28.8 (d, J C-P = 2.3 z), 33.9 (d, J C-P = 5.2 z), 123.2, 125.9, 128.5, 128.6, 129.1, 131.3, 131.9, 132.1, 132.5, 133.9, 134.2, 136.9; 31 P NMR ( Mz, CDCl 3, TMS): δ 44.54; MS (ESI) m/z (%): 379 (100) [M + +1]; RMS (MALDI) Calcd. for C PS +1 (M + +1) requires , Found:
15 Se PPh 2 2m Diphenylphosphinoselenoic acid Se-(4-m-tolyl-but-3-enyl) ester 2m. A colorless oil; IR (C 2 Cl 2 ): ν 3054, 3023, 2932, 1597, 1493, 1437, 1363, 1198, 1114, 1096, 1071, 1027, 998, 754, 696, 538 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.49 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.90 (2,dt, J = 7.2, 7.5 z, C 2 ), 5.97 (1, t, J = 7.2 z, =C), (16, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 24.9 (d, J C-P = 1.8 z), 30.5 (d, J C-P = 4.8 z), 127.0, 127.1, 128.0, 128.2, 128.5, 128.7, 129.7, 131.1, 132.1, 133.5, 134.8, 139.5, 142.1, 143.5; 31 P NMR (75 Mz, CDCl 3, TMS): δ 41.18; MS (ESI) m/z (%): 489 (100) [M + +1]; RMS (MALDI) Calcd. for C PSe +1 (M + +1) requires , Found:
16 Se PPh 2 2n Diphenylphosphinoselenoic acid Se-[4,4-bis(4-chlorophenyl)but-3-enyl] ester 2n. A yellow oil; IR (C 2 Cl 2 ): ν 3052, 2919, 1511, 1481, 1437, 1199, 1113, 1096, 1070, 1021, 821, 696, 539 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.30 (3, s, C 3 ), 2.37 (3, s, C 3 ), 2.48 (2,dt, J = 7.2, 7.2 z, C 2 ), 2.89 (2, dt, J = 7.2, 7.2 z,c 2 ), 5.90 (1, t, J = 7.2 z, =C), (8, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 21.0, 21.2, 25.0 (d, J C-P = 2.3 z), 30.5 (d, J C-P = 4.1 z), 125.9, 127.1, 128.4, 128.6, 128.8, 129.5, 131.2, 132.0, 133.5, 134.8, 136.5, 136.7, 139.5, 143.2; 31 P NMR (75 Mz, CDCl 3, TMS): δ 41.22; MS (ESI) m/z (%): 517 (23) [M + +1]; RMS (MALDI) Calcd. for C PNaSe +1 (M + +Na) requires , Found:
17 Cl Cl 2o Se PPh 2 Diphenylphosphinoselenoic acid Se-[4,4-bis(4-chlorophenyl)but-3-enyl] ester (2o). A yellow oil; IR (C 2 Cl 2 ): ν 3056, 2930, 1590, 1491, 1437, 1400, 1263, 1198, 1092, 1070, 1014, 831, 721, 696, 539 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.47 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.91 (2, dt, J = 7.2, 7.2 z,c 2 ), 5.97 (1, t, J = 7.2 z, =C), 7.0 (2, d, J = 8.4 z, Ar), 7.06 (2, d, J = 8.1 z, Ar), 7.21 (2, d, J = 8.1 z, Ar), 7.31 (2, d, J = 8.4 z, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 24.5 (d, J C-P = 2.3 z), 30.7 (d, J C-P = 4.0 z), 127.3, 128.3, 128.5, 128.7, 131.0, 131.3, 132.3, 132.4, 133.2, 133.3, 133.8, 137.4, 140.1, 141.5; 31 P NMR ( Mz, CDCl 3, TMS): δ 41.12; MS (MALDI) m/z (%): 557 (100) [M + +1]; RMS (MALDI) Calcd. for C Cl 2 PSe +1 (M + ) requires , Found:
18 2p (E-) Se PPh 2 Diphenylphosphinoselenoic acid Se-(4-phenylbut-3-enyl) ester (2p). A yellow solid, m.p o C; IR (C 2 Cl 2 ): ν 3056, 3025, 1589, 1492, 1437, 1196, 1113, 1096, 1070, 1027, 966, 696, 539 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.59 (2, dt, J = 7.2, 7.2 z, C 2 ), 2.96 (2, dt, J = 7.2, 7.2 z, C 2 ), 6.09 (1, dt, J = 7.2, 15.6 z, =C), 6.35 (1, d, J = 15.6 z, =C), (5, m, Ar), (6, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 24.6 (d, J C-P = 2.7 z), 34.1 (d, J C-P =3.7 z), 126.1, 128.0, 128.5, 128.7, 131.1, 131.3, 131.9, 132.2, 132.3, 137.1; 31 P NMR ( Mz, CDCl 3, TMS): δ 41.16; MS (ESI) m/z (%): 429 (100) [M + +17]; RMS (MALDI) Calcd. for C PSe +1 (M + +1) requires , Found:
19 PPh 2 3a Diphenylphosphinic acid 4,4-diphenylbut-3-enyl ester (3a). A colorless oil; IR (C 2 Cl 2 ): ν 3056, 3025, 1593, 1494, 1439, 1228, 1130, 1113, 1012, 996, 697, 561 cm -1 ; 1 NMR (300 Mz, CDCl 3, TMS): δ 2.55 (2, dt, J = 6.3, 6.3 z, C 2 ), 4.10 (2, dt, J = 6.3, 6.3 z, C 2 ), 6.08 (1, t, J = 6.3 z, =C), (16, m, Ar), (4, m, Ar); 13 C NMR (75 Mz, CDCl 3, TMS): δ 31.0 (d, J C-P = 6.8 z), 64.2 (d, J C-P = 7.8 z), 124.1, 127.0, 127.2, 128.0, 128.3, 128.5, 130.3, 131.5, 131.6, 132.0, 132.1, 139.5, 142.1, 144.2; 31 P NMR ( Mz, CDCl 3, TMS): δ 32.79; MS (ESI) m/z (%): 425 (18) [M + +1]; RMS (MALDI) Calcd. for C PNa +1 (M + +Na) requires , Found:
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