578:
495:). In this case, the intermediate vinyl cation is formed by addition of HCl because it is resonance-stabilized by the phenyl group. Nevertheless, the lifetime of this high energy species is short, and the resulting vinyl cation-chloride anion ion pair immediately collapses, before the chloride ion has a chance to leave the solvent shell, to give the vinyl chloride. The proximity of the anion to the side of the vinyl cation where the proton was added is used to rationalize the observed predominance of
213:
355:
466:
446:("addition, electrophilic, third-order"). Because the simultaneous collision of three chemical species in a reactive orientation is improbable, the termolecular transition state is believed to be reached when the nucleophile attacks a reversibly-formed weak association of the alkyne and HCl. Such a mechanism is consistent with the predominantly
503:
615:
OH) is produced. The "spare" hydrogen atom from the water goes into "replacing" the "lost" hydrogen and, thus, reproduces sulfuric acid. Another pathway in which water molecule combines directly to the intermediate carbocation (lower way) is also possible. This pathway become predominant when aqueous
425:
mechanism (described in more detail for alkynes, below), in which transfer of the proton and nucleophilic addition occur in a concerted manner. The extent to which each pathway contributes depends on the several factors like the nature of the solvent (e.g., polarity), nucleophilicity of the halide
705:
electrophiles effect asymmetric selenenylation reactions. The reagents are aryl selenenyl bromides, and they were first developed for solution phase chemistry and then modified for solid phase bead attachment via an aryloxy moiety. The solid-phase reagents were applied toward the selenenylation of
437:
In the case of dialkyl-substituted alkynes (e.g., 3-hexyne), the intermediate vinyl cation that would result from this process is highly unstable. In such cases, the simultaneous protonation (by HCl) and attack of the alkyne by the nucleophile (Cl) is believed to take place. This mechanistic
1737:
Olah, George A.; Germain, Alain; Lin, Henry C.; Forsyth, David A. (1975). "Electrophilic reactions at single bonds. XVIII. Indication of protosolvated de facto substituting agents in the reactions of alkanes with acetylium and nitronium ions in superacidic media".
1037:. In this sense the electrophilicity index is a kind of electrophilic power. Correlations have been found between electrophilicity of various chemical compounds and reaction rates in biochemical systems and such phenomena as allergic contact dermititis.
680:
389:
of the product, that is, from which side Cl will attack relies on the types of alkenes applied and conditions of the reaction. At least, which of the two carbon atoms will be attacked by H is usually decided by
1571:
Davis, F. A.; Kumar, A.; Chen, B. C. (1991). "Chemistry of oxaziridines. 16. A short, highly enantioselective synthesis of the AB-ring segments of Ξ³-rhodomycionone and Ξ±-citromycinone using (+)-oxaziridine".
349:. For example, the reaction of HCl with ethylene furnishes chloroethane. The reaction proceeds with a cation intermediate, being different from the above halogen addition. An example is shown below:
1508:
Mootz, Dietrich; Deeg, Axel (July 1992). "2-Butyne and hydrogen chloride cocrystallized: solid-state geometry of Cl-H.cntdot..cntdot..cntdot..pi. hydrogen bonding to the carbon-carbon triple bond".
878:
978:
413:(HBr) also takes this pathway, but sometimes a radical process competes and a mixture of isomers may form. Although introductory textbooks seldom mentions this alternative, the Ad
1426:
Fahey, Robert C.; Lee, Do-Jae. (April 1968). "Polar additions to olefins and acetylenes. V. Bimolecular and termolecular mechanisms in the hydrochlorination of acetylenes".
1702:
De
Vleeschouwer, Freija; Speybroeck, Veronique Van; Waroquier, Michel; Geerlings, Paul; De Proft, Frank (2007). "Electrophilicity and Nucleophilicity Index for Radicals".
1044:. Strongly electrophilic radicals such as the halogens react with electron-rich reaction sites, and strongly nucleophilic radicals such as the 2-hydroxypropyl-2-yl and
1494:
1412:
927:
902:
1358:
1031:
1002:
1242:
Lenoir, D.; Chiappe, C. (2003). "What is the Nature of the First-Formed
Intermediates in the Electrophilic Halogenation of Alkenes, Alkynes, and Allenes?".
394:. Thus, H attacks the carbon atom that carries fewer substituents so as the more stabilized carbocation (with the more stabilizing substituents) will form.
1278:
Brown, R. S. (1997). "Investigation of the Early Steps in
Electrophilic Bromination through the Study of the Reaction with Sterically Encumbered Olefins".
1067:. Superelectrophiles form as a doubly electron deficient superelectrophile by protosolvation of a cationic electrophile. As observed by Olah, a mixture of
426:
ion, stability of the carbocation, and steric effects. As brief examples, the formation of a sterically unencumbered, stabilized carbocation favors the Ad
1802:
Lin King, John V.; Emrick, Joshua J.; Kelly, Mark J. S.; Herzig, Volker; King, Glenn F.; Medzihradszky, Katalin F.; Julius, David (5 September 2019).
1740:
1545:
710:
hydride reducing agents. Solid-supported reagents offers advantages over solution phase chemistry due to the ease of workup and purification.
1334:
462:. In support of the proposed alkyne-HCl association, a T-shaped complex of an alkyne and HCl has been characterized crystallographically.
1921:
1140:) superelectrophiles, charged centers are separated by no more than one atom, for example, the protonitronium ion O=N=OβH (a protonated
1388:
1189:
1766:
Solingapuram Sai, Kiran Kumar; Gilbert, Thomas M.; Klumpp, Douglas A. (2007). "Knorr
Cyclizations and Distonic Superelectrophiles".
1470:
589:
H molecule has a Ξ΄+ charge on the initial H atom. This is attracted to and reacts with the double bond in the same way as before.
333:
if the alkene has a cation-stabilizing substituent like phenyl group. There is an example of the isolation of the bromonium ion
577:
837:
1280:
1244:
1768:
1574:
1104:
143:
409:(HF) and hydrogen iodide (HI) react with alkenes in a similar manner, and Markovnikov-type products will be given.
58:, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.
160:
1543:
Wang, Z.; Tu, Y.; Frohn, M.; Zhang, J.; Shi, Y. (1997). "An
Efficient Catalytic Asymmetric Epoxidation Method".
655:
942:
706:
various alkenes with good enantioselectivities. The products can be cleaved from the solid support using
1092:
1005:
636:
362:
Proton (H) adds (by working as an electrophile) to one of the carbon atoms on the alkene to form cation
66:
529:. This reaction occurs in a similar way to the addition reaction but has an extra step in which the OSO
391:
1059:
are defined as cationic electrophilic reagents with greatly enhanced reactivities in the presence of
569:
does take part in the overall reaction, however it remains unchanged so is classified as a catalyst.
1148:
superelectrophiles, they are separated by 2 or more atoms, for example, in the fluorination reagent
1126:
260:
132:
1859:
Zhao, Jianhua; Lin King, John V.; Paulsen, Candice E.; Cheng, Yifan; Julius, David (2020-07-08).
1488:
1406:
1352:
820:
Several methods exist to rank electrophiles in order of reactivity and one of them is devised by
518:
354:
212:
458:
for the example shown) of the hydrochlorination product and the termolecular rate law, Rate =
267:
configuration. When other nucleophiles such as water or alcohol are existing, these may attack
1898:
1880:
1841:
1823:
1784:
1719:
1684:
1640:
1617:
1525:
1476:
1466:
1443:
1394:
1384:
1340:
1330:
1260:
1080:
1072:
929:
905:
691:
406:
386:
346:
306:
242:
The alkene is working as an electron donor and bromine as an electrophile. The three-membered
176:
98:
86:
70:
62:
911:
886:
1888:
1872:
1831:
1815:
1776:
1748:
1711:
1676:
1648:
1609:
1582:
1553:
1517:
1435:
1288:
1252:
784:
410:
39:
694:
effect enantioselective ketone alpha oxidation en route to the AB-ring segments of various
1197:
695:
651:
345:
Hydrogen halides such as hydrogen chloride (HCl) adds to alkenes to give alkyl halides in
310:
116:
55:
1015:
986:
483:("addition, electrophilic, second-order, ion pair") mechanism to give predominantly the
225:
The electrophilic Br-Br molecule interacts with electron-rich alkene molecule to form a
1893:
1860:
1836:
1803:
1064:
933:
774:
264:
1804:"A Cell-Penetrating Scorpion Toxin Enables Mode-Specific Modulation of TRPA1 and Pain"
1915:
1377:
1141:
522:
326:
243:
47:
259:
The bromonium ion is opened by the attack of Br from the back side. This yields the
1600:
Uehlin, L.; Wirth, T. (2001). "Novel
Polymer-Bound Chiral Selenium Electrophiles".
1100:
1041:
764:
90:
78:
1218:
434:
3 pathway to a greater extent compared to reactions involving the chloride ion.
1164:
1149:
1068:
821:
687:
597:
94:
82:
43:
1819:
1876:
1668:
1383:. Richardson, Kathleen Schueller. (3rd ed.). New York: Harper & Row.
1045:
226:
124:
51:
1884:
1827:
1529:
1480:
1447:
1344:
17:
1398:
1084:
1076:
1060:
707:
673:
249:
consisted of two carbon atoms and a bromine atom forms with a release of Br.
167:
against a sample to deduce the number of double bonds present. For example,
164:
31:
1902:
1845:
1788:
1723:
1688:
1666:
Chattaraj, P. K.; Sarkar, U.; Roy, D. R. (2006). "Electrophilicity Index".
1621:
1264:
1256:
465:
1324:
1305:
In analogy to aromatic substitution, this process has also been termed an
627:, whose purposes include fuels and starting material for other chemicals.
325:
will appear when the Br is large excess in the reaction medium. A Ξ²-bromo
1861:"Irritant-evoked activation and calcium modulation of the TRPA1 receptor"
1638:
Parr, R. G.; Szentpaly, L. v.; Liu, S. (1999). "Electrophilicity Index".
734:
724:
702:
647:
526:
302:
294:
102:
1752:
1586:
1521:
1439:
620:
Overall, this process adds a molecule of water to a molecule of ethene.
1096:
1034:
794:
744:
643:
624:
172:
128:
120:
109:
74:
1780:
1715:
1680:
1652:
1613:
1557:
1292:
679:
654:. The catalyst can accomplish highly enantioselective epoxidations of
501:
464:
804:
754:
665:
661:
286:
168:
136:
159:
These occur between alkenes and electrophiles, often halogens as in
1172:, the sensory neural target for electrophilic irritants in mammals.
27:
A chemical species that accepts an electron pair from a nucleophile
1169:
1048:
radical react with a preference for electron-poor reaction sites.
828:
669:
502:
600:, forming ethyl hydrogensulphate (upper way on the above scheme).
317:) also react through similar pathways. The direct conversion of
1009:
430:
2 pathway, while a more nucleophilic bromide ion favors the Ad
1463:
Perspectives on structure and mechanism in organic chemistry
639:. Typically chiral electrophiles are also optically pure.
1323:
Vollhardt, K. Peter C.; Schore, Neil Eric (January 2014).
623:
This is an important reaction in industry, as it produces
932:. This equation is related to the classical equation for
533:
H group is replaced by an OH group, forming an alcohol:
61:
Electrophiles mainly interact with nucleophiles through
717:
1018:
989:
945:
914:
889:
873:{\displaystyle \omega ={\frac {\chi ^{2}}{2\eta }}\,}
840:
683:
Use of a chiral oxaziridine for asymmetric synthesis.
163:. Common reactions include use of bromine water to
50:. Because electrophiles accept electrons, they are
1376:
1025:
996:
972:
921:
896:
872:
698:, including Ξ³-rhodomycionone and Ξ±-citromycinone.
207:This takes the form of 3 main steps shown below;
1326:Organic chemistry : structure and function
676:form before proceeding in the catalytic cycle.
607:O) is added and the mixture heated, ethanol (C
417:2 mechanism is generally competitive with the
8:
1493:: CS1 maint: multiple names: authors list (
1411:: CS1 maint: multiple names: authors list (
69:reactions. Frequently seen electrophiles in
1465:(2nd ed.). Hoboken, N.J.: John Wiley.
369:Chloride ion (Cl) combines with the cation
329:intermediate may be predominant instead of
285:("addition, electrophilic, second-order").
123:, chemical species that do not satisfy the
1357:: CS1 maint: location missing publisher (
1063:. These compounds were first described by
1040:An electrophilicity index also exists for
1892:
1835:
1379:Mechanism and theory in organic chemistry
1022:
1017:
993:
988:
969:
958:
952:
944:
918:
913:
893:
888:
869:
853:
847:
839:
472:In contrast, phenylpropyne reacts by the
238:Forming of a three-membered bromonium ion
1510:Journal of the American Chemical Society
1428:Journal of the American Chemical Society
678:
101:, polarizable neutral molecules such as
1633:
1631:
1181:
1129:via the protonated nitronium dication.
1125:only in presence of a strong acid like
1486:
1404:
1350:
973:{\displaystyle P={\frac {V^{2}}{R}}\,}
814:Some selected values (no dimensions)
592:The remaining (negatively charged) OSO
85:, polarized neutral molecules such as
1075:is able to remove a hydride ion from
572:This is the reaction in more detail:
438:pathway is known by the Ingold label
7:
1370:
1368:
650:-derived organocatalyst used in the
54:. Most electrophiles are positively
660:-disubstituted and trisubstituted
25:
1190:"Nucleophiles and Electrophiles"
668:, is oxidized by stoichiometric
576:
353:
211:
271:to give an alcohol or an ether.
135:, and some Lewis acids such as
1329:(7th ed.). New York, NY.
397:This is another example of an
1:
1095:is the dication. Likewise,
341:Addition of hydrogen halides
1461:A., Carroll, Felix (2010).
1105:nitronium tetrafluoroborate
637:chiral and optically stable
596:H ion then attaches to the
1938:
1922:Physical organic chemistry
1820:10.1016/j.cell.2019.07.014
1375:H., Lowry, Thomas (1987).
1219:"Electrophile | chemistry"
161:halogen addition reactions
1877:10.1038/s41586-020-2480-9
813:
1091:and HF. The responsible
517:One of the more complex
255:Attacking of bromide ion
1223:Encyclopedia Britannica
1083:via the formation of a
922:{\displaystyle \eta \,}
897:{\displaystyle \chi \,}
719:Electrophilicity index
635:Many electrophiles are
277:This process is called
1257:10.1002/chem.200390097
1027:
998:
974:
923:
898:
874:
826:electrophilicity index
714:Electrophilicity scale
692:N-sulfonyloxaziridines
684:
664:. The Shi catalyst, a
616:sulfuric acid is used.
506:
469:
221:Forming of a Ο-complex
42:that forms bonds with
1093:reactive intermediate
1028:
999:
975:
924:
899:
875:
701:Polymer-bound chiral
682:
561:As can be seen, the H
505:
468:
1814:(6): 1362β1374.e16.
1194:butane.chem.uiuc.edu
1016:
987:
943:
912:
887:
838:
385:In this manner, the
373:to form the adducts
155:Addition of halogens
1753:10.1021/ja00843a067
1587:10.1021/jo00003a042
1552:(46): 11224β11235.
1522:10.1021/ja00040a077
1440:10.1021/ja01010a034
1127:fluorosulfuric acid
1099:can be nitrated to
1079:when combined with
1026:{\displaystyle V\,}
997:{\displaystyle R\,}
720:
519:hydration reactions
450:addition (>15:1
1057:Superelectrophiles
1052:Superelectrophiles
1023:
994:
970:
919:
894:
870:
718:
685:
631:Chiral derivatives
507:
470:
392:Markovnikov's rule
263:dibromide with an
99:carbonyl compounds
1871:(7823): 141β145.
1781:10.1021/jo7013092
1775:(25): 9761β9764.
1747:(10): 2928β2929.
1741:J. Am. Chem. Soc.
1716:10.1021/ol071038k
1710:(14): 2721β2724.
1681:10.1021/cr040109f
1653:10.1021/ja983494x
1641:J. Am. Chem. Soc.
1614:10.1021/ol0164435
1608:(18): 2931β2933.
1558:10.1021/ja972272g
1546:J. Am. Chem. Soc.
1516:(14): 5887β5888.
1336:978-1-4641-2027-5
1293:10.1021/ar960088e
1081:hydrofluoric acid
1073:boron trifluoride
967:
930:chemical hardness
906:electronegativity
867:
818:
817:
407:Hydrogen fluoride
387:stereoselectivity
347:hydrohalogenation
309:cation (Hg), and
177:1,2-dibromoethane
150:Organic chemistry
71:organic syntheses
16:(Redirected from
1929:
1907:
1906:
1896:
1856:
1850:
1849:
1839:
1799:
1793:
1792:
1763:
1757:
1756:
1734:
1728:
1727:
1699:
1693:
1692:
1675:(6): 2065β2091.
1663:
1657:
1656:
1647:(9): 1922β1924.
1635:
1626:
1625:
1597:
1591:
1590:
1581:(3): 1143β1145.
1568:
1562:
1561:
1540:
1534:
1533:
1505:
1499:
1498:
1492:
1484:
1458:
1452:
1451:
1434:(8): 2124β2131.
1423:
1417:
1416:
1410:
1402:
1382:
1372:
1363:
1362:
1356:
1348:
1320:
1314:
1303:
1297:
1296:
1275:
1269:
1268:
1251:(5): 1036β1044.
1239:
1233:
1232:
1230:
1229:
1215:
1209:
1208:
1206:
1205:
1196:. Archived from
1186:
1124:
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1115:
1114:
1032:
1030:
1029:
1024:
1003:
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1000:
995:
979:
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934:electrical power
928:
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868:
866:
858:
857:
848:
785:Carbon disulfide
721:
696:natural products
580:
411:Hydrogen bromide
357:
215:
119:such as organic
117:oxidizing agents
46:by accepting an
40:chemical species
21:
1937:
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1281:Acc. Chem. Res.
1277:
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849:
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716:
690:such as chiral
652:Shi epoxidation
633:
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509:
487:product (~10:1
481:
477:
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311:dichlorocarbene
300:
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113:
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28:
23:
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5:
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1500:
1471:
1453:
1418:
1390:978-0060440848
1389:
1364:
1335:
1315:
1308:
1298:
1287:(3): 131β137.
1270:
1234:
1210:
1180:
1178:
1175:
1174:
1173:
1167:
1160:
1157:
1151:
1120:
1111:
1088:
1065:George A. Olah
1053:
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1021:
992:
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815:
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775:Sulfur dioxide
771:
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747:
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731:
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672:to the active
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367:
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265:antiperiplanar
252:
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217:
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111:
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26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1934:
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1769:J. Org. Chem.
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327:carbenium ion
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284:
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266:
262:
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244:bromonium ion
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688:Oxaziridines
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67:substitution
60:
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1311:2 mechanism
1165:Nucleophile
1069:acetic acid
822:Robert Parr
598:carbocation
405:mechanism.
283:2 mechanism
52:Lewis acids
1669:Chem. Rev.
1228:2020-09-21
1204:2020-09-21
1177:References
1061:superacids
1046:tert-butyl
1012:or Ξ©) and
1006:resistance
831:given as:
499:addition.
305:ion (RS),
125:octet rule
1885:1476-4687
1828:1097-4172
1704:Org. Lett
1602:Org. Lett
1530:0002-7863
1489:cite book
1481:286483846
1448:0002-7863
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1353:cite book
1345:866584251
1150:F-TEDA-BF
1085:superacid
1077:isobutane
916:η
891:χ
864:η
851:χ
842:ω
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708:organotin
674:dioxirane
642:One such
585:The HβOSO
521:utilises
513:Hydration
227:Ο-complex
32:chemistry
1916:Category
1903:32641835
1846:31447178
1789:17999519
1724:17559221
1689:16771443
1622:11529793
1399:14214254
1265:12596140
1159:See also
1146:distonic
1134:gitionic
735:Chlorine
725:Fluorine
703:selenium
648:fructose
527:catalyst
303:sulfenyl
295:chlorine
133:radicals
129:carbenes
127:such as
121:peracids
77:such as
73:include
63:addition
1894:7483980
1837:6731142
1138:gitonic
1097:methane
1087:from BF
1035:voltage
1004:is the
795:Benzene
745:Bromine
662:alkenes
646:is the
644:reagent
625:ethanol
307:mercury
261:vicinal
173:bromine
165:titrate
75:cations
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1865:Nature
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755:Iodine
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169:ethene
97:, and
1170:TRPA1
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883:with
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799:1.45
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779:2.01
769:2.52
759:3.09
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670:oxone
657:trans
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313:(:CCl
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1785:PMID
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1071:and
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