287:. Some however proceed by metal-phosphinidene intermediates, i.e. species with M=PR double bonds. One such example is the Ti-catalyzed hydrophosphination of diphenylacetylene with phenylphosphine. This system involves a cationic catalyst precursor that is stabilized by the bulky 2,4,6-tri(isopropyl)phenyl- substituent on the phosphinidene and the close ionic association of methyltris(pentafluorophenyl)borate. This precursor undergoes exchange with phenylphosphine to give the titanium-phenylphosphinidene complex, which is the catalyst. The Ti=PPh species undergoes a cycloaddition with diphenylacetylene to make the corresponding metallacyclobutene. The substrate, phenylphosphine, protonolyzes the Ti-C bond and after a proton shift regenerates the catalyst and releases the new phosphine.
17:
220:
327:
319:
253:
461:
Douglass, M. R.; Ogasawara, M.; Hong, S.; Metz, M. V.; Marks, T. J. (2002). ""Widening the Roof": Synthesis and
Characterization of New ChiralC1-Symmetric Octahydrofluorenyl Organolanthanide Catalysts and Their Implementation in the Stereoselective Cyclizations of Aminoalkenes and Phosphinoalkenes".
1216:
Zhao, G.; Basuli, F.; Kilgore, U. J.; Fan, H.; Aneetha, H.; Huffman, J. C.; Wu, G.; Mindiola, D. J. (2006). "Neutral and
Zwitterionic Low-Coordinate Titanium Complexes Bearing the Terminal Phosphinidene Functionality. Structural, Spectroscopic, Theoretical, and Catalytic Studies Addressing the Ti−P
505:
Scriban, C.; Glueck, D. S.; Zakharov, L. N.; Kassel, W. S.; Dipasquale, A. G.; Golen, J. A.; Rheingold, A. L. (2006). "P−C and C−C Bond
Formation by Michael Addition in Platinum-Catalyzed Hydrophosphination and in the Stoichiometric Reactions of Platinum Phosphido Complexes with Activated Alkenes".
279:
or alkyne inserts into the Ln-P bond. Finally, protonolysis of the Ln-C bond with the starting primary phosphine releases the new phosphine and regenerates the catalyst. Given that the metal is electron-poor, the M-C bond is sufficiently enough to be protonolyzed by the substrate primary phosphine.
39:
bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is influenced by the catalyst. Catalysts take many forms, but most prevalent are bases and free-radical initiators. Most hydrophosphinations involve reactions of
338:
of a P-H bond. For example, a Pt(0) catalyst undergoes oxidative addition of a secondary phosphine to form the corresponding hydrido Pt(II) phosphido complex. These systems catalyze hydrophosphination of acrylonitrile, although this reaction can be achieved without metal catalysts. The key P-C
342:
The usual mechanism for hydrophosphination for late metal catalysts involves insertion of the alkene into the metal-phosphorus bond. Insertion into the metal-hydrogen bond is also possible. The product phosphine is produced through reductive elimination of a P-C bond rather than a P-H bond in
227:
The reactions proceed by abstraction of an H atom the phosphine precursor, producing the phosphino radical, a seven electron species. This radical then adds to the alkene, and subsequent H-atom transfer completes the cycle. Some highly efficient hydrophosphinations appear not to proceed via
670:
Xu, C.; Jun Hao
Kennard, G.; Hennersdorf, F.; Li, Y.; Pullarkat, S. A.; Leung, P. H. (2012). "Chiral Phosphapalladacycles as Efficient Catalysts for the Asymmetric Hydrophosphination of Substituted Methylidenemalonate Esters: Direct Access to Functionalized Tertiary Chiral Phosphines".
570:
Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. (2000). "Pt(Me-Duphos)-Catalyzed
Asymmetric Hydrophosphination of Activated Olefins: Enantioselective Synthesis of Chiral Phosphines".
314:
Late transition metal hydrophosphination catalysts, i.e. those reliant on the nickel-triad and neighboring elements, generally require alkenes and alkynes with electron withdrawing substituents. A strong base is required as a cocatalyst.
692:
Huang, Y.; Pullarkat, S. A.; Teong, S.; Chew, R. J.; Li, Y.; Leung, P. H. (2012). "Palladacycle-Catalyzed
Asymmetric Intermolecular Construction of Chiral Tertiary P-Heterocycles by Stepwise Addition of H–P–H Bonds to Bis(enones)".
527:
Scriban, C.; Kovacik, I.; Glueck, D. S. (2005). "A Protic
Additive Suppresses Formation of Byproducts in Platinum-Catalyzed Hydrophosphination of Activated Olefins. Evidence for P−C and C−C Bond Formation by Michael Addition".
483:
Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. (2003). "Homoleptic
Lanthanide Alkyl and Amide Precatalysts Efficiently Mediate Intramolecular Hydrophosphination/Cyclization. Observations on Scope and Mechanism".
410:
Douglass, M. R.; Stern, C. L.; Marks, T. J. (2001). "Intramolecular
Hydrophosphination/Cyclization of Phosphinoalkenes and Phosphinoalkynes Catalyzed by Organolanthanides: Scope, Selectivity, and Mechanism".
1357:
Han, Li-Biao; Ono, Yutaka; Xu, Qing; Shimada, Shigeru (2010). "Highly
Selective Markovnikov Addition of Hypervalent H-Spirophosphoranes to Alkynes Mediated by Palladium Acetate: Generality and Mechanism".
1322:
Kazankova, M. A.; Shulyupin, M. O.; Borisenko, A. A.; Beletskaya, I. P. (2002). "Synthesis of Alkyl(diphenyl)phosphines by Hydrophosphination of Vinylarenes Catalyzed by Transition Metal Complexes".
389:
Motta, A.; Fragalà, I. L.; Marks, T. J. (2005). "Energetics and Mechanism of Organolanthanide-Mediated Phosphinoalkene Hydrophosphination/Cyclization. A Density Functional Theory Analysis".
714:
Huang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P. H. (2012). "Palladacycle-Catalyzed Asymmetric Hydrophosphination of Enones for Synthesis of C*- and P*-Chiral Tertiary Phosphines".
1181:
Trifonov, A. A.; Basalov, I. V.; Kissel, A. A. (2016). "Use of organolanthanides in the catalytic intermolecular hydrophosphination and hydroamination of multiple C–C bonds".
549:
Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. (1997). "Platinum-Catalyzed Acrylonitrile Hydrophosphination via Olefin Insertion into a Pt−P Bond".
641:
Huang, Y.; Pullarkat, S. A.; Li, Y.; Leung, P. H. (2010). "Palladium(ii)-catalyzed asymmetric hydrophosphination of enones: Efficient access to chiral tertiary phosphines".
236:
Metal-catalyzed hydrophosphinations are not widely used, although they have been extensively researched. Studies mainly focus on secondary and primary organophosphines (R
440:
Douglass, M. R.; Marks, T. J. (2000). "Organolanthanide-Catalyzed Intramolecular Hydrophosphination/Cyclization of Phosphinoalkenes and Phosphinoalkynes".
351:
Utilizing phosphorus(V) precursors hydrophosphorylation entails the insertion of alkenes and alkynes into the P-H bonds of secondary phosphine oxides:
264:
configurations are effective catalysts for hydrophosphinations of simple alkenes and alkynes. Intramolecular reactions are facile, e.g. starting with
855:
Gibson, G. L.; Morrow, K. M. E.; McDonald, R.; Rosenberg, L. (2011). "Diastereoselective synthesis of a "chiral-at-Ru" secondary phosphine complex".
1008:
Alonso, Francisco; Moglie, Yanina; Radivoy, Gabriel; Yus, Miguel (2012). "Solvent- and catalyst-free regioselective hydrophosphanation of alkenes".
343:
Glueck's system. The Ni(0) catalyst involves oxidation addition of a P-H bond to the metal, followed by insertion of the alkene into the M-H bond.
244:, respectively). These substrates bind to metals, and the resulting adducts insert alkenes and alkynes into the P-H bonds via diverse mechanisms.
797:
Derrah, E. J.; Pantazis, D. A.; McDonald, R.; Rosenberg, L. (2010). "Concerted Cycloaddition of Alkenes to a Ruthenium-Phosphorus Double Bond".
776:
Derrah, E. J.; Pantazis, D. A.; McDonald, R.; Rosenberg, L. (2007). "A Highly Reactive Ruthenium Phosphido Complex Exhibiting Ru−P π-Bonding".
1102:
284:
929:
Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. (1999). "Phosphine in the synthesis of organophosphorus compounds".
906:
743:
Huang, Y.; Chew, R. J.; Li, Y.; Pullarkat, S. A.; Leung, P. H. (2011). "Direct Synthesis of Chiral Tertiary Diphosphinesvia
1252:
Perrier, A.; Comte, V.; Moïse, C.; Le Gendre, P. (2010). "First Titanium-Catalyzed 1,4-Hydrophosphination of 1,3-Dienes".
612:; Togni, A. (2005). "Enantioselective Addition of Secondary Phosphines to Methacrylonitrile: Catalysis and Mechanism".
1390:
108:
Acid catalysis is applicable to hydrophosphination with alkenes that form stable carbocations. These alkenes include
1400:
275:
with the bis(trimethylsilyl)methylene ligand forming the lanthanide-phosphido complex. Subsequently, the pendant
69:
1395:
256:
Mechanism proposed for intramolecular hydrophosphination of α, ω-pentenylphosphine catalyzed by lanthanocenes.
201:
1405:
1287:
Shulyupin, M. O.; Kazankova, M. A.; Beletskaya, I. P. (2002). "Catalytic Hydrophosphination of Styrenes".
193:
145:
269:
1045:
Greenberg, S.; Stephan, D. W. (2008). "Stoichiometric and catalytic activation of P–H and P–P bonds".
938:
826:
Derrah, E. J.; McDonald, R.; Rosenberg, L. (2010). "The cycloaddition of alkynes at a Ru–P π-bond".
998:
Quin, L. D. A Guide to Organophosphorus Chemistry; John Wiley & Sons: New York, 2000; pp 28-29.
592:
Pringle, P. G.; Smith, M. B. (1990). "Platinum(0)-catalysed hydrophosphination of acrylonitrile".
1339:
1119:
Rosenberg, L. (2013). "Mechanisms of Metal-Catalyzed Hydrophosphination of Alkenes and Alkynes".
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Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2006). "Phosphorus Compounds, Organic".
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Bange, Christine A.; Waterman, Rory (2016). "Challenges in Catalytic Hydrophosphination".
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942:
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958:
65:
1343:
950:
379:
The reaction can be effected both using metal catalysts or free-radical initiators.
189:
1085:
Glueck, David S. (2010). "Recent Advances in Metal-Catalyzed C–P Bond Formation".
898:
322:
Mechanism proposed for hydrophosphination catalyzed by a Pt(II) phosphido complex.
1094:
609:
109:
28:
1335:
972:
King, R. Bruce (1972). "Poly(tertiary Phosphines) and Their Metal Complexes".
868:
326:
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catalyst. In the first step, the Ti(II) precursor inserted in the P-H bond of
32:
53:
41:
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601:
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bond-forming step occurs through an outer-sphere, Michael-type addition.
213:
209:
197:
36:
985:
330:
Mechanism proposed for hydrophosphination catalyzed by a Ni(0) catalyst.
1194:
1030:
1021:
654:
1300:
1230:
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789:
760:
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684:
625:
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541:
519:
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402:
1089:. Topics in Organometallic Chemistry. Vol. 31. pp. 65–100.
1058:
839:
318:
252:
325:
317:
251:
218:
52:
The usual application of hydrophosphination involves reactions of
15:
290:
Titanium-catalyzed 1,4-hydrophosphination of 1,3-dienes with
747:(II)-Catalyzed Asymmetric Hydrophosphination of Dienones".
334:
Some late metal hydrophosphination catalysts proceed via
594:
Journal of the Chemical Society, Chemical Communications
268:-pentenylphosphine. The primary phosphine undergoes a
208:
and trioctylphosphine are prepared in good yields from
144:
Bases catalyze the addition of secondary phosphines to
283:
Most metal catalyzed hydrophosphinations proceed via
228:
radicals, but alternative explanations are lacking.
188:Many hydrophosphination reactions are initiated by
294:has been demonstrated. It is a rare example of a
60:). Typically base-catalysis allows addition of
248:Early transition metal and lanthanide catalysts
891:Ullmann's Encyclopedia of Industrial Chemistry
8:
204:. In this way, the commercially important
1117:Rosenberg, L. R. ACS Catal. 2013, 3, 2845.
347:Hydrophosphorylation and related reactions
1360:Bulletin of the Chemical Society of Japan
1029:
924:
922:
920:
918:
1219:Journal of the American Chemical Society
1080:
1078:
1076:
614:Journal of the American Chemical Society
551:Journal of the American Chemical Society
442:Journal of the American Chemical Society
413:Journal of the American Chemical Society
881:
799:Angewandte Chemie International Edition
7:
1324:Russian Journal of Organic Chemistry
200:are typical initiators, as well as
14:
20:Hydrophosphination of an alkene.
951:10.1070/RC1999v068n03ABEH000464
310:Late transition metal catalysts
1254:Chemistry – A European Journal
1148:Chemistry - A European Journal
1:
974:Accounts of Chemical Research
899:10.1002/14356007.a19_545.pub2
285:metal phosphido intermediates
1095:10.1007/978-3-642-12073-2_4
223:Radical hydrophosphination.
29:carbon-carbon multiple bond
1422:
869:10.1016/j.ica.2010.12.058
232:Metal-catalyzed reactions
70:tris(cyanoethyl)phosphine
1047:Chemical Society Reviews
931:Russian Chemical Reviews
1336:10.1023/A:1022552404812
857:Inorganica Chimica Acta
828:Chemical Communications
643:Chemical Communications
202:Ultraviolet irradiation
1266:10.1002/chem.200901863
1160:10.1002/chem.201602749
811:10.1002/anie.201000356
331:
323:
257:
224:
146:vinyldiphenylphosphine
27:is the insertion of a
21:
1372:10.1246/bcsj.20100141
329:
321:
255:
222:
19:
602:10.1039/C39900001701
184:Free-radical methods
140:(R = Me, alkyl, etc)
112:and many analogues:
1189:(48): 19172–19193.
1183:Dalton Transactions
1154:(36): 12598–12605.
986:10.1021/ar50053a003
943:1999RuCRv..68..215T
716:Inorganic Chemistry
620:(48): 17012–17024.
419:(42): 10221–10238.
260:Metal complexes of
1391:Addition reactions
1195:10.1039/C6DT03913H
1087:C-X Bond Formation
1022:10.1039/c2gc35898k
655:10.1039/C0CC00925C
336:oxidative addition
332:
324:
258:
225:
25:Hydrophosphination
22:
1301:10.1021/ol017238s
1231:10.1021/ja064853o
1133:10.1021/cs400685c
1127:(12): 2845–2855.
1104:978-3-642-12072-5
834:(25): 4592–4594.
805:(19): 3367–3370.
790:10.1021/om0700056
761:10.1021/ol202480r
728:10.1021/ic202472f
707:10.1021/om300405h
685:10.1021/om201115n
626:10.1021/ja0555163
585:10.1021/om990882e
563:10.1021/ja970355r
542:10.1021/om050433g
520:10.1021/om060631n
498:10.1021/om030439a
476:10.1021/om0104013
454:10.1021/ja993633q
425:10.1021/ja010811i
403:10.1021/om050570d
300:diphenylphosphine
292:diphenylphosphine
206:tributylphosphine
62:Michael acceptors
1413:
1401:Organophosphanes
1376:
1375:
1366:(9): 1086–1099.
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1348:
1347:
1319:
1313:
1312:
1284:
1278:
1277:
1249:
1243:
1242:
1225:(41): 13575–85.
1217:Multiple Bond".
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1143:
1137:
1136:
1115:
1109:
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1059:10.1039/B612306F
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840:10.1039/C002765K
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273:-bond metathesis
216:, respectively.
48:Acid-base routes
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1010:Green Chemistry
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749:Organic Letters
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713:
695:Organometallics
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673:Organometallics
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573:Organometallics
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508:Organometallics
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486:Organometallics
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391:Organometallics
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383:Further reading
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277:terminal alkene
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980:(5): 177–185.
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755:(21): 5862–5.
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649:(37): 6950–2.
638:
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190:free-radicals
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84:=CHZ → P(CH
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66:acrylonitrile
63:
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26:
18:
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1330:(10): 1479.
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1295:(5): 761–3.
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1288:
1282:
1260:(1): 64–67.
1257:
1253:
1247:
1222:
1218:
1211:
1186:
1182:
1176:
1151:
1147:
1141:
1124:
1120:
1113:
1086:
1050:
1046:
1040:
1016:(10): 2699.
1013:
1009:
1003:
994:
977:
973:
967:
934:
930:
890:
884:
860:
856:
831:
827:
802:
798:
781:
777:
752:
748:
744:
719:
715:
701:(13): 4871.
698:
694:
676:
672:
646:
642:
617:
613:
610:Sadow, A. D.
596:(23): 1701.
593:
576:
572:
557:(21): 5039.
554:
550:
536:(21): 4871.
533:
529:
514:(24): 5757.
511:
507:
492:(23): 4630.
489:
485:
467:
463:
445:
441:
416:
412:
397:(21): 4995.
394:
390:
378:
359:P(O)H + CH
350:
341:
333:
313:
295:
289:
282:
270:
265:
261:
259:
235:
226:
187:
143:
107:
100:, CN, C(O)NH
51:
24:
23:
1031:11336/95357
863:: 133–139.
784:(6): 1473.
679:(8): 3022.
448:(8): 1824.
363:=CHR → R
110:isobutylene
1385:Categories
908:3527306730
877:References
579:(6): 950.
470:(2): 283.
240:PH and RPH
33:phosphorus
959:250775640
198:peroxides
54:phosphine
42:phosphine
1344:94929172
1309:11869121
1274:19918817
1239:17031972
1203:27891536
1168:27405918
1067:18648674
848:20458386
819:20358572
769:21985055
736:22289417
663:20730193
634:16316248
433:11603972
214:1-octene
210:1-butene
68:to give
64:such as
37:hydrogen
939:Bibcode
96:(Z = NO
80:+ 3 CH
44:(PH3).
31:into a
1342:
1307:
1272:
1237:
1201:
1166:
1101:
1065:
957:
905:
846:
817:
767:
734:
661:
632:
431:
367:P(O)CH
160:=CHPR'
1340:S2CID
955:S2CID
306:PH).
164:→ R
156:+ CH
1305:PMID
1270:PMID
1235:PMID
1199:PMID
1164:PMID
1099:ISBN
1063:PMID
903:ISBN
844:PMID
815:PMID
765:PMID
732:PMID
659:PMID
630:PMID
429:PMID
212:and
196:and
194:AIBN
136:)CPH
128:→ R
124:C=CH
120:+ R
1368:doi
1332:doi
1297:doi
1262:doi
1227:doi
1223:128
1191:doi
1156:doi
1129:doi
1091:doi
1055:doi
1026:hdl
1018:doi
982:doi
947:doi
895:doi
865:doi
861:369
836:doi
807:doi
786:doi
757:doi
724:doi
703:doi
681:doi
651:doi
622:doi
618:127
598:doi
581:doi
559:doi
555:119
538:doi
516:doi
494:doi
472:doi
450:doi
446:122
421:doi
417:123
399:doi
302:(Ph
266:α,ω
192:.
176:PR'
168:PCH
152:HPR
132:(CH
56:(PH
1387::
1364:83
1362:.
1338:.
1328:38
1326:.
1303:.
1291:.
1268:.
1258:16
1256:.
1233:.
1221:.
1197:.
1187:45
1185:.
1162:.
1152:22
1150:.
1123:.
1097:.
1075:^
1061:.
1051:37
1049:.
1024:.
1014:14
1012:.
976:.
953:.
945:.
935:68
933:.
917:^
901:.
893:.
859:.
842:.
832:46
830:.
813:.
803:49
801:.
782:26
780:.
763:.
753:13
751:.
745:Pd
730:.
720:51
718:.
699:31
697:.
677:31
675:.
657:.
647:46
645:.
628:.
616:.
577:19
575:.
553:.
534:24
532:.
512:25
510:.
490:22
488:.
468:21
466:.
444:.
427:.
415:.
395:24
393:.
371:CH
172:CH
148::
116:PH
92:Z)
88:CH
76:PH
72::
1374:.
1370::
1346:.
1334::
1311:.
1299::
1293:4
1276:.
1264::
1241:.
1229::
1205:.
1193::
1170:.
1158::
1135:.
1131::
1125:3
1107:.
1093::
1069:.
1057::
1034:.
1028::
1020::
988:.
984::
978:5
961:.
949::
941::
911:.
897::
871:.
867::
850:.
838::
821:.
809::
792:.
788::
771:.
759::
738:.
726::
709:.
705::
687:.
683::
665:.
653::
636:.
624::
604:.
600::
587:.
583::
565:.
561::
544:.
540::
522:.
518::
500:.
496::
478:.
474::
456:.
452::
435:.
423::
405:.
401::
375:R
373:2
369:2
365:2
361:2
357:2
355:R
304:2
296:d
271:σ
262:d
242:2
238:2
178:2
174:2
170:2
166:2
162:2
158:2
154:2
138:2
134:3
130:2
126:2
122:2
118:3
104:)
102:2
98:2
94:3
90:2
86:2
82:2
78:3
58:3
35:-
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