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613:
1256:; Ford, J. Gair; Fonguerna, Sílvia; Adams, Harry; Jones, Ray V. H.; Fieldhouse, Robin (1998-08-08). "Catalytic Asymmetric Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in Sulfur Ylide Epoxidations with Chiral 1,3-Oxathianes".
449:
Use of a sulfoxonium allows more facile preparation of the reagent using weaker bases as compared to sulfonium ylides. (The difference being that a sulfoxonium contains a doubly bonded oxygen whereas the sulfonium does not.) The former react slower due to their increased stability. In addition, the
852:
variants, but the substrate scope is still limited in all cases. The catalytic variants have been developed almost exclusively for enantioselective purposes; typical organosulfide reagents are not prohibitively expensive and the racemic reactions can be carried out with equimolar amounts of ylide
694:
studies suggests an irreversible 1,4-attack leading to the cyclopropane is energetically favored versus a reversible 1,2-attack that would lead to the epoxide. With extended conjugated systems 1,6-addition tends to predominate over 1,4-addition. Many electron-withdrawing groups have been shown
963:
to form the epoxide. Since the factors underlying these desiderata are at odds, tuning of the catalyst properties has proven difficult. Shown below are several of the most successful catalysts along with the yields and enantiomeric excess for their use in synthesis of
441:
Many types of ylides can be prepared with various functional groups both on the anionic carbon center and on the sulfur. The substitution pattern can influence the ease of preparation for the reagents (typically from the sulfonium halide, e.g.
1508:
Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. (1996). "Total
Synthesis of Baccatin III and Taxol".
947:
Catalytic reagents have been less successful, with most variations suffering from poor yield, poor enantioselectivity, or both. There are also issues with substrate scope, most having limitations with methylene transfer and
689:
states that it is because sulfoxonium reagents have a less concentrated negative charge on the carbon atom (softer), so it prefers 1,4-attack on the softer nucleophilic site. Another explanation supported by
424:
well beyond the original publications. It has seen use in a number of high-profile total syntheses, as detailed below, and is generally recognized as a powerful transformative tool in the organic repertoire.
484:. These, similarly to sulfoxonium reagents, react much slower and are typically easier to prepare. These are limited in their usefulness as the reaction can become prohibitively sluggish: examples involving
209:
failed and a benzalfluorene oxide was obtained instead, noting that "reaction between the sulfur ylid and benzaldehydes did not afford benzalfluorenes as had the phosphorus and arsenic ylids."
213:
375:
The degree of reversibility in the initial step (and therefore the diastereoselectivity) depends on four factors, with greater reversibility corresponding to higher selectivity:
570:
are by far the most common application of the
Johnson–Corey–Chaykovsky reaction. Examples involving complex substrates and 'exotic' ylides have been reported, as shown below.
1569:"Understanding Regioselectivities of Corey–Chaykovsky Reactions of Dimethylsulfoxonium Methylide (DMSOM) and Dimethylsulfonium Methylide (DMSM) toward Enones: A DFT Study"
420:
The application of the
Johnson–Corey–Chaykovsky reaction in organic synthesis is diverse. The reaction has come to encompass reactions of many types of sulfur ylides with
1494:
1003:
853:
without raising costs significantly. Chiral sulfides, on the other hand, are more costly to prepare, spurring the advancement of catalytic enantioselective methods.
1709:
397:
with greater hindrance leading to greater reversibility by disfavoring formation of the intermediate and slowing the rate-limiting rotation of the central bond.
193:
below). Additionally detailed below are the history, mechanism, scope, and enantioselective variants of the reaction. Several reviews have been published.
1131:; Winn, C. L. (2004). "Catalytic, Asymmetric Sulfur Ylide-Mediated Epoxidation of Carbonyl Compounds: Scope, Selectivity, and Applications in Synthesis".
775:
934:
367:
1173:
Gololobov, Y. G.; Nesmeyanov, A. N.; lysenko, V. P.; Boldeskul, I. E. (1987). "Twenty-five years of dimethylsulfoxonium ethylide (corey's reagent)".
895:
1511:
1258:
919:
are easily synthesized, although the yields are lower than for the oxathiane reagent. The ylide conformation is determined by interaction with the
1084:; Richardson, J. (2003). "The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions".
668:
730:
971:
819:
326:
1538:
Kuehne, M. E.; Xu, F. (1993). "Total synthesis of strychnan and aspidospermatan alkaloids. 3. The total synthesis of (.+-.)-strychnine".
743:
In addition to the reactions originally reported by
Johnson, Corey, and Chaykovsky, sulfur ylides have been used for a number of related
1408:
Kawashima, T.; Okazaki, R. (1996). "Synthesis and
Reactions of the Intermediates of the Wittig, Peterson, and their Related Reactions".
840:, which is labelled as "ee") variant of the Johnson–Corey–Chaykovsky reaction remains an active area of academic research. The use of
815:
as the catalyst and (dimethyloxosulfaniumyl)methanide as the monomer have been reported for the synthesis of various complex polymers.
1478:
1451:
590:
1540:
983:
1699:
682:
523:=H). The substitution pattern on aryl reagents can heavily influence the selectivity of the reaction as per the criteria above.
1714:
249:) by Corey and Chaykovsky as efficient methylene-transfer reagents established the reaction as a part of the organic canon.
1326:
Johnson, A.W.; LaCount, R.B. (1961). "The
Chemistry of Ylids. VI. Dimethylsulfonium Fluorenylide—A Synthesis of Epoxides".
1647:
1133:
411:
with greater solvation allowing more facile rotation in the betaine intermediate, lowering the amount of reversibility.
1704:
892:
and approach of the aldehyde is limited to one face of the ylide by steric interactions with the methyl substituents.
799:
653:
tolerance to the carbonyl equivalent. The examples shown below are representative; in the latter, an aziridine forms
1209:(1997). "Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and Rearrangement".
979:
Aggarwal has developed an alternative method employing the same sulfide as above and a novel alkylation involving a
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602:
477:
73:
691:
620:
443:
353:
201:
The original publication by
Johnson concerned the reaction of 9-dimethylsulfonium fluorenylide with substituted
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159:
685:
is typically obtained with sulfoxonium reagents than with sulfonium reagents. One explanation based on the
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with higher stability leading to greater reversibility by favoring the starting material over the betaine.
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is another important application of the
Johnson–Corey–Chaykovsky reaction and provides an alternative to
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1043:
912:
841:
808:
744:
361:
270:
57:
446:) and overall reaction rate in various ways. The general format for the reagent is shown on the right.
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observed results from the reversibility of the initial addition, allowing equilibration to the favored
252:
869:(DCI) but is limited by the availability of only one enantiomer of the reagent. The synthesis of the
612:
543:
457:
of sulfoxonium reagents are greatly preferred to the significantly more toxic, volatile, and odorous
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182:
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861:
The most successful reagents employed in a stoichiometric fashion are shown below. The first is a
767:. The long reaction times required for these reactions prevent them from occurring as significant
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1608:"Opportunities for the Application and Advancement of the Corey–Chaykovsky Cyclopropanation"
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variants of the reaction (See
Variations below). The size of the groups can also influence
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206:
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530:. The size of the alkyl groups are the major factors in selectivity with these reagents.
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If the ylide carbon is substituted with an alkyl group the reagent is referred to as an
845:
716:
1473:(2 ed.). Hoboken, New Jersey: John Wiley & Sons, Inc. pp. 174–175, 743.
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chiral catalyst with carbenoid alkylation for the
Johnson–Corey–Chaykovsky reaction
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betaine. Initial addition of the ylide results in a betaine with adjacent charges;
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115:
118:. It was discovered in 1961 by A. William Johnson and developed significantly by
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720:
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589:
The reaction has been used in a number of notable total syntheses including the
312:
163:
119:
865:
oxathiane that has been employed in the synthesis of the β-adrenergic compound
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The vast majority of reagents are monosubstituted at the ylide carbon (either R
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1684:
1645:
Luo, J.; Shea, K. J. (2010). "Polyhomologation. A Living C1 Polymerization".
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649:. Though less widely applied, the reaction has a similar substrate scope and
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as hydrogen). Disubstituted reagents are much rarer but have been described:
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sulfide that efficiently generates the ylide which can also act as a good
779:
Oxetane and Azitidine synthesis with the Johnson–Corey–Chaykovsky reaction
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862:
563:
278:
131:
1553:
1467:
Mundy, Bradford, P.; Ellerd, Michael D.; Favaloro, Frank G. Jr. (2005).
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1394:
1340:
938:
chiral camphor-derived reagent for the Johnson–Corey–Chaykovsky reaction
492:
and virtually no examples involving other EWG's. For these, the related
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McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.;
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511:. These have been developed extensively, second only to the classical
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the reaction serves as a ring-expansion to produce the corresponding
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309:
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127:
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The subsequent development of (dimethyloxosulfaniumyl)methanide, (CH
122:
and Michael Chaykovsky. The reaction involves addition of a sulfur
1446:. Hoboken, New Jersey: John Wiley & Sons, Inc. pp. 2–14.
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899:
chiral oxathiane reagent for the Johnson–Corey–Chaykovsky reaction
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hydrogens and approach of the aldehyde is blocked by the camphor
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with higher stability similarly leading to greater reversibility.
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is rotation of the central bond into the conformer necessary for
1567:
Xiang, Yu; Fan, Xing; Cai, Pei‐Jun; Yu, Zhi‐Xiang (2019-01-23).
500:
992:. The method too has limited substrate scope, failing for any
142:
to produce the corresponding 3-membered ring. The reaction is
1357:; Chaykovsky, M. (1965). "Dimethyloxosulfonium Methylide ((CH
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Living polymerization with Johnson–Corey–Chaykovsky Reaction
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Cyclopropanation with the Johnson–Corey–Chaykovsky reaction
185:
transfer, and to this end has been used in several notable
975:
chiral catalysts for the Johnson–Corey–Chaykovsky reaction
848:
fashion has proved more successful than the corresponding
217:
The first example of the Johnson–Corey–Chaykovsky reaction
538:, have been used to synthesize reagents that can perform
672:
Aziridination with the Johnson–Corey–Chaykovsky reaction
181:
The reaction is most often employed for epoxidation via
323:
takes place through a 4-membered cyclic intermediate.
269:
for the Johnson–Corey–Chaykovsky reaction consists of
150:
substitution in the product regardless of the initial
1606:
Beutner, Gregory L.; George, David T. (2023-01-20).
1381:). Formation and Application to Organic Synthesis".
371:
Selectivity in the Johnson–Corey–Chaykovsky reaction
330:Mechanism of the Johnson–Corey–Chaykovsky reaction
300:it gets expelled forming the ring. In the related
1470:Name Reactions and Reagents in Organic Chemistry
727:and even some electron deficient heterocycles.
681:For addition of sulfur ylides to enones, higher
285:group. A negative charge is transferred to the
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1493:: CS1 maint: multiple names: authors list (
1289:(2007). "Chalcogenides as Organocatalysts".
803:cycloaddition with Corey–Chaykovsky reagent
499:If the ylide carbon is substituted with an
476:If the ylide carbon is substituted with an
1612:Organic Process Research & Development
771:when synthesizing epoxides and aziridines.
488:are widespread, with many fewer involving
190:
31:
1443:Named Reactions in Heterocyclic Chemistry
877:which reduces the nucleophilicity of the
873:diastereomer is rationalized via the 1,3-
1512:Journal of the American Chemical Society
1259:Journal of the American Chemical Society
955:. The trouble stems from the need for a
931:base to promote formation of the ylide.
1060:
695:promote the cyclopropanation including
507:group, the reagent is referred to as a
480:(EWG), the reagent is referred to as a
233:and (dimethylsulfaniumyl)methanide, (CH
158:via this method serves as an important
1486:
1369:) and Dimethylsulfonium Methylide ((CH
27:Chemical reaction in organic chemistry
1573:European Journal of Organic Chemistry
996:possessing basic substituents due to
461:by-products from sulfonium reagents.
304:, the formation of the much stronger
7:
1710:Carbon-carbon bond forming reactions
401:Solvation of charges in the betaine
437:General form of ylide reagent used
35:Johnson-Corey–Chaykovsky reaction
25:
603:Kuehne Strychnine total synthesis
591:Danishefsky Taxol total synthesis
585:Example 1 of epoxidation with CCR
577:Example 1 of epoxidation with CCR
356:calculations have shown that the
177:Johnson–Corey–Chaykovsky Reaction
88:Johnson–Corey–Chaykovsky reaction
1541:The Journal of Organic Chemistry
558:Reactions of sulfur ylides with
795:equivalent" have been reported.
788:wherein the ylide serves as a "
692:density functional theory (DFT)
162:alternative to the traditional
907:-derived reagent developed by
707:(the example below involves a
496:is typically more appropriate.
90:(sometimes referred to as the
18:Dimethyloxosulfonium methylide
1:
1648:Accounts of Chemical Research
1189:10.1016/s0040-4020(01)86869-1
1134:Accounts of Chemical Research
903:The other major reagent is a
624:Strychnine synthesis CCR step
605:which produces the pesticide
888:of the ylide is limited by
828:Enantioselective variations
205:derivatives. The attempted
1736:
1685:Animation of the mechanism
1049:Strychnine total synthesis
677:Synthesis of cyclopropanes
661:to form the corresponding
478:electron-withdrawing group
380:Stability of the substrate
927:. The reaction employs a
444:trimethylsulfonium iodide
354:density functional theory
247:Corey–Chaykovsky reagents
92:Corey–Chaykovsky reaction
80:
74:corey-chaykovsky-reaction
69:Organic Chemistry Portal
63:
34:
1624:10.1021/acs.oprd.2c00315
616:Taxol synthesis CCR step
256:Corey–Chaykovsky Reagent
1205:Li, A.-H.; Dai, L.-X.;
1087:Chemical Communications
998:competitive consumption
857:Stoichiometric reagents
629:Synthesis of aziridines
319:formation and instead,
1700:Ring forming reactions
1585:10.1002/ejoc.201801216
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832:The development of an
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1440:Li, Jack Jie (2005).
1254:Aggarwal, Varinder K.
1044:Taxol total synthesis
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867:dichloroisoproterenol
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554:Synthesis of epoxides
509:semi-stabilized ylide
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271:nucleophilic addition
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191:Synthesis of epoxides
176:
106:for the synthesis of
58:Ring forming reaction
544:diastereoselectivity
339:diastereoselectivity
207:Wittig-like reaction
1554:10.1021/jo00078a030
1418:10.1055/s-1996-5540
1395:10.1021/ja01084a034
1341:10.1021/ja01463a040
890:transannular strain
838:enantiomeric excess
659:nucleophilic attack
154:. The synthesis of
49:Michael Chaykovsky
43:A. William Johnson
1705:Addition reactions
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1000:of the carbenoid.
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364:on the sulfonium.
358:rate-limiting step
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267:reaction mechanism
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144:diastereoselective
1661:10.1021/ar100062a
1655:(11): 1420–1433.
1548:(26): 7490–7497.
1525:10.1021/ja952692a
1519:(12): 2843–2859.
1329:J. Am. Chem. Soc.
1305:10.1021/cr068402y
1299:(12): 5841–5883.
1272:10.1021/ja9812150
1266:(33): 8328–8339.
1225:10.1021/cr960411r
1183:(12): 2609–2651.
1147:10.1021/ar030045f
1090:(21): 2644–2651.
909:Varinder Aggarwal
633:The synthesis of
104:organic chemistry
100:chemical reaction
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46:Elias James Corey
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482:stabilized ylide
452:dialkylsulfoxide
393:Steric hindrance
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1618:(1): 10–41.
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978:
966:(E)-stilbene
957:nucleophilic
946:
902:
886:conformation
866:
860:
831:
790:nucleophilic
742:
721:phosphonates
717:nitro groups
680:
654:
647:oxaziridines
632:
588:
557:
550:substrates.
533:
527:
508:
481:
463:
448:
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385:
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349:
342:
335:
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264:
246:
220:
203:benzaldehyde
200:
180:
147:
95:
91:
87:
85:
64:Identifiers
40:Named after
29:
1176:Tetrahedron
1029:Epoxidation
929:phosphazene
917:enantiomers
725:isocyanides
687:HSAB theory
515:reagents (R
455:by-products
405:counterions
321:olefination
313:double bond
164:epoxidation
120:E. J. Corey
1694:Categories
1056:References
1039:E.J. Corey
921:bridgehead
879:equatorial
757:aziridines
635:aziridines
607:strychnine
601:, and the
306:phosphorus
296:is a good
287:heteroatom
245:(known as
112:aziridines
1632:1083-6160
1593:1434-193X
1489:cite book
984:carbenoid
953:aldehydes
950:aliphatic
882:lone pair
850:catalytic
793:carbenoid
765:azetidine
564:aldehydes
548:alicyclic
513:methylene
348:over the
315:prevents
291:sulfonium
261:Mechanism
183:methylene
146:favoring
1669:20825177
1313:18072810
1233:11848902
1155:15311960
1104:14649793
1012:See also
863:bicyclic
784:Several
753:epoxides
713:sulfones
568:epoxides
566:to form
407:such as
279:carbonyl
156:epoxides
132:aldehyde
108:epoxides
102:used in
1410:Synlett
989:in situ
986:formed
981:rhodium
968:oxide.
915:. Both
911:of the
905:camphor
761:oxetane
697:ketones
655:in situ
560:ketones
536:methyls
409:lithium
346:betaine
317:oxirane
277:to the
273:of the
197:History
168:olefins
98:) is a
1667:
1630:
1591:
1477:
1450:
1311:
1231:
1153:
1102:
925:moiety
884:. The
842:chiral
811:using
705:amides
701:esters
639:imines
490:esters
486:amides
310:oxygen
294:cation
128:ketone
114:, and
1034:Ylide
871:axial
751:With
663:amine
643:amine
637:from
599:taxol
597:drug
505:allyl
416:Scope
336:trans
283:imine
275:ylide
189:(See
148:trans
140:enone
138:, or
136:imine
126:to a
124:ylide
1665:PMID
1628:ISSN
1589:ISSN
1577:2019
1495:link
1475:ISBN
1448:ISBN
1365:SOCH
1309:PMID
1229:PMID
1151:PMID
1100:PMID
755:and
562:and
501:aryl
468:or R
343:anti
334:The
265:The
229:SOCH
86:The
1657:doi
1620:doi
1581:doi
1550:doi
1521:doi
1517:118
1414:doi
1391:doi
1377:SCH
1337:doi
1301:doi
1297:107
1268:doi
1264:120
1221:doi
1185:doi
1143:doi
1092:doi
763:or
711:),
546:in
503:or
403:by
350:syn
281:or
241:SCH
96:CCR
94:or
1696::
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1614:.
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1491:}}
1487:{{
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1307:.
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1179:.
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1137:.
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723:,
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715:,
703:,
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519:=R
170:.
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1371:3
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1223::
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1187::
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1145::
1106:.
1094::
521:2
517:1
470:2
466:1
308:-
243:2
239:2
237:)
235:3
231:2
227:2
225:)
223:3
20:)
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