374:
438:
700:
733:
726:
636:
594:
620:
670:
799:
269:
2056:
2080:
297:
494:
2068:
995:, many perfluorinated compounds are prepared by electrochemical synthesis, which is conducted in liquid HF at voltages near 5–6 V using Ni anodes. The method was invented in the 1930s. Amines, alcohols, carboxylic acids, and sulfonic acids are converted to perfluorinated derivatives using this technology. A solution or suspension of the hydrocarbon in
213:
The potential drop between the electrodes determines the rate constant of the reaction. Electrosynthesis is carried out with either constant potential or constant current. The reason one chooses one over the other is due to a trade-off of ease of experimental conditions versus current efficiency.
222:
around the electrode). This is not the case under constant current conditions, however. Instead, as the substrate's concentration decreases the potential across the cell increases in order to maintain the fixed reaction rate. This consumes current in side reactions produced outside the target
198:
take place at the anode. Compounds are reduced at the cathode. Radical intermediates are often invoked. The initial reaction takes place at the surface of the electrode and then the intermediates diffuse into the solution where they participate in secondary reactions.
179:. The purpose of the divided cell is to permit the diffusion of ions while restricting the flow of the products and reactants. This separation simplifies workup. An example of a reaction requiring a divided cell is the reduction of
125:
or tetrabutylammonium salts. The choice of electrodes with respect to their composition and surface area can be decisive. For example, in aqueous conditions the competing reactions in the cell are the formation of
138:
anode and lead cathode could be used effectively because of their high overpotentials for oxygen and hydrogen formation respectively. Many other materials can be used as electrodes. Other examples include
373:
163:
or lead. Cell designs can be undivided cell or divided cell type. In divided cells the cathode and anode chambers are separated with a semiporous membrane. Common membrane materials include
437:
1508:
1455:
Cardoso, D. S.; Šljukić, B.; Santos, D. M.; Sequeira, C. A. (17 July 2017). "Organic
Electrosynthesis: From Laboratorial Practice to Industrial Applications".
1898:
1817:
Lee, Byungik; Naito, Hiroto; Nagao, Masahiro; Hibino, Takashi (9 July 2012). "Alternating-Current
Electrolysis for the Production of Phenol from Benzene".
1457:
214:
Constant potential uses current more efficiently because the current in the cell decreases with time due to the depletion of the substrate around the
1041:
Sperry, Jeffrey B.; Wright, Dennis L. (2006). "The application of cathodic reductions and anodic oxidations in the synthesis of complex molecules".
243:
1986:
210:
consumed in forming the products to the total number of
Coulombs passed through the cell. Side reactions decrease the current efficiency.
1188:
1021:
577:
511:
1308:
1286:
1484:
1891:
619:
1782:
B. Innocent; et al. (February 2009). "Electro-reduction of carbon dioxide to formate on lead electrode in aqueous medium".
1941:
558:
1535:
Krishnan, V.; Muthukumaran, A.; Udupa, H. V. K. (1979). "The electroreduction of benzyl cyanide on iron and cobalt cathodes".
428:
1436:
530:
515:
1255:
Schäfer, H. J.; Feldhues, U. (1982). "Oxidation of
Primary Aliphatic Amines to Nitriles at the Nickel Hydroxide Electrode".
635:
2111:
2072:
770:
537:
1727:
Bouwman, Elisabeth; Angamuthu, Raja; Byers, Philip; Lutz, Martin; Spek, Anthony L. (15 July 2010). "Electrocatalytic CO
2121:
2060:
2041:
1884:
1852:
Simons, J. H. (1949). "Production of
Fluorocarbons I. The Generalized Procedure and its Use with Nitrogen Compounds".
1008:
156:
593:
2116:
1971:
826:
715:
in good yield. At higher negative reduction potentials, the nitroalkene can be reduced further, giving the primary
325:
for instance in the electrosynthesis of the tetramethyl ester of ethanetetracarboxylic acid from the corresponding
544:
504:
2106:
1976:
1921:
833:
348:
1951:
992:
1675:
669:
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2016:
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2031:
1981:
660:
268:
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Wessling, M.; Schäfer, H.J. (1991). "Cathodic reduction of 1-nitroalkenes to oximes and primary amines".
2026:
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332:
172:
90:
732:
725:
1946:
1926:
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1392:"Beyond traditional synthesis: Electrochemical approaches to amine oxidation for nitriles and imines"
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38:
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431:, an alcohol could be almost instantaneously deoxygenated by electroreducing its toluate ester.
2006:
2001:
1996:
1931:
1834:
1756:
1700:
1625:
1432:
1373:
1326:
Hampson, N; Lee, J; MacDonald, K (1972). "The oxidation of amino compounds at anodic silver".
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22:
1645:"Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung"
2036:
777:
762:
606:
236:, in which two carboxylic acids decarboxylate, and the remaining structures bond together:
219:
152:
118:
53:. Electrosynthesis is actively studied as a science and also has industrial applications.
1870:
See also related articles by Simons et al. on pages 53, 55, 59, and 64 of the same issue.
1356:
Barba, Fructuoso; Batanero, Belen (2004). "Paired
Electrosynthesis of Cyanoacetic Acid".
1173:
1744:
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2011:
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159:. Some reactions use a sacrificial electrode that is consumed during the reaction like
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is electrolyzed at 5–6 V to produce high yields of the perfluorinated product.
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1078:(Topics in Current Chemistry, Vol. 148) E. Steckhan (Ed), Springer, NY
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678:
400:
340:
207:
98:
82:
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187:, where the latter chemical is susceptible to oxidation at the anode.
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1054:
404:
127:
94:
1683:(2nd ed.). London: Macmillan and Co. Limited. pp. 102–104.
1644:
1503:
258:(nitrogen or oxygen) is present at the α-position. The intermediate
651:, was at one time an important method for the synthesis of certain
276:
Anodic electrosynthesis oxidize primary aliphatic amine to nitrile.
202:
The yield of an electrosynthesis is expressed both in terms of the
716:
712:
682:
279:
479:
of activated olefins is applied industrially in the synthesis of
845:
160:
106:
1880:
1419:
487:
101:-water solvent mixtures with an electrolyte such as a soluble
1485:"Electrochemistry Encyclopedia – Tafel: his life and science"
1175:
Electrochemical
Reactions and Mechanisms in Organic Chemistry
1141:
Utley, James (1997). "Trends in
Organic Electrosynthesis".
1094:"Synthetic Organic Electrochemistry: Calling All Engineers"
918:
and oxygen is evolved at the anode, the total reaction is:
206:
and current efficiency. Current efficiency is the ratio of
113:. Aprotic conditions often use an organic solvent such as
16:
Synthesis of chemical compounds in an electrochemical cell
1206:"Electrode Materials in Modern Organic Electrochemistry"
832:
It has been reported that formate can be formed by the
1076:
Topics in current chemistry. Electrochemistry, Vol. 3
792:, shows as the rare aldehyde form) in a divided cell:
1608:(13 June 2007). "Transformation of Carbon dioxide".
286:-acyliminium ions, which can be captured by various
1914:
1287:"Coll. Vol. 7, p.307 (1990); Vol. 63, p.206 (1985)"
518:. Unsourced material may be challenged and removed.
1504:"Vollständige Reduktion des Benzylacetessigesters"
1309:"Coll. Vol. 7, p.482 (1990); Vol. 60, p.78 (1981)"
605:to the 1,4-dihydro derivatives is similar to a
218:(stirring is usually necessary to decrease the
1649:Berichte der Deutschen Chemischen Gesellschaft
1509:Berichte der deutschen chemischen Gesellschaft
1421:Ullmann's Encyclopedia of Industrial Chemistry
821:An electrocatalysis by a copper complex helps
609:. Examples from industry are the reduction of
1892:
685:in a divided cell; the cathodic reduction of
262:is trapped by a nucleophile, usually solvent.
45:, electrosynthesis sometimes offers improved
8:
1731:Conversion to Oxalate by a Copper Complex".
1351:
1349:
1204:Heard, D. M.; Lennox, A.J.J. (6 July 2020).
1092:Yan, M.; Kawamata, Y.; Baran, P. S. (2017).
399:have been developed in the last decades for
1616:(6). American Chemical Society: 2365–2387.
1450:
1448:
1899:
1885:
1877:
1643:Tafel, Julius; Friedrichs, Gustav (1904).
1458:Organic Process Research & Development
1166:
1164:
1403:
1231:
1221:
1117:
578:Learn how and when to remove this message
69:The basic setup in electrosynthesis is a
1179:. Amsterdam: Elsevier Science. pp.
941:
937:
924:
914:
894:
890:
867:
468:
464:
460:
1819:Angewandte Chemie International Edition
1210:Angewandte Chemie International Edition
1098:Angewandte Chemie International Edition
1033:
308:. An example is the α-methoxylation of
1854:Journal of the Electrochemical Society
413:is prepared commercially by oxidizing
97:conditions often use alcohol-water or
232:A well-known electrosynthesis is the
7:
2067:
810:could be prepared from reduction of
516:adding citations to reliable sources
1784:Journal of Applied Electrochemistry
1537:Journal of Applied Electrochemistry
151:(as a liquid pool in the reactor),
1502:Tafel, Julius; Hahl, Hans (1907).
827:uses carbon dioxide as a feedstock
14:
2078:
2066:
2055:
2054:
1358:The Journal of Organic Chemistry
825:to oxalic acid; this conversion
797:
731:
724:
698:
668:
659:, a reaction accompanied by the
634:
618:
592:
492:
436:
372:
295:
267:
241:
503:needs additional citations for
304:This reaction type is called a
134:at the cathode. In this case a
1020:Electrochemistry Encyclopedia
968:An electrosynthesis employing
626:and the reduction of 2-methoxy
1:
1405:10.1021/acsorginorgau.4c00025
355:anodes (the latter is formed
1340:10.1016/0013-4686(72)90014-X
771:supercritical carbon dioxide
677:The cathodic reduction of a
449:is prepared from dimerizing
2042:Volume combustion synthesis
1677:Practical Organic Chemistry
1009:Electrochemical engineering
463:=CHCN + 2 e + 2 H → NC(CH
384:from cathodic reduction of
157:reticulated vitreous carbon
2138:
1972:Enantioselective synthesis
1715:, vol. 1, p. 311
984:
976:the cathode and the anode.
601:The cathodic reduction of
395:Selective electrochemical
250:A variation is called the
121:with electrolytes such as
2050:
1977:Fully automated synthesis
1922:Artificial gene synthesis
1796:10.1007/s10800-008-9658-4
1661:10.1002/cber.190403703116
1522:10.1002/cber.190704003102
834:electrochemical reduction
475:In practice,the cathodic
349:oxidative decarboxylation
1952:Custom peptide synthesis
1694:A. W. Ingersoll (1929).
1584:10.1002/cber.19911241024
1471:10.1021/acs.oprd.7b00004
1429:10.1002/14356007.a05_235
1171:Grimshaw, James (2000).
1143:Chemical Society Reviews
993:organofluorine chemistry
829:to generate oxalic acid.
776:Cathodic reduction of a
707:Cathodic reduction of a
483:from two equivalents of
388:and anodic oxidation of
312:-carbomethoxypyrrolidine
1753:10.1126/science.1177981
1674:Cohen, Julius (1920) .
1423:. Weinheim: Wiley-VCH.
961:of acetonitrile afford
747:electrosynthesis using
429:Markó–Lam deoxygenation
89:combinations minimizes
41:. Compared to ordinary
2032:Solvothermal synthesis
1982:Hydrothermal synthesis
1831:10.1002/anie.201202159
1223:10.1002/anie.202005745
1110:10.1002/anie.201707584
957:of carbon dioxide and
661:rearrangement reaction
2027:Solid-phase synthesis
1315:on 26 September 2007.
1293:on 26 September 2007.
823:reduce carbon dioxide
719:but with lower yield.
417:at a lead electrode..
173:polytetrafluoroethene
91:electrical resistance
2112:Industrial processes
1947:Convergent synthesis
1927:Biomimetic synthesis
1696:"Hydrocinnamic acid"
1269:10.1055/s-1982-29721
1183:–7, 282, & 310.
1155:10.1039/cs9972600157
808:phenylpropanoic acid
512:improve this article
59:wastewater treatment
39:electrochemical cell
1962:Divergent synthesis
1745:2010Sci...327..313A
1598:Sakakura, Toshiyasu
1491:on 6 February 2012.
1328:Electrochimica Acta
1216:(43): 18866–18884.
987:Electrofluorination
981:Electrofluorination
972:prepares phenol at
970:alternating current
754:An electrochemical
663:of the alkyl group:
645:Tafel rearrangement
422:Cathodic reductions
282:can be oxidized to
185:phenylhydroxylamine
123:lithium perchlorate
2122:Chemical synthesis
1908:Chemical synthesis
1549:10.1007/BF00610957
955:Cathodic reduction
769:is promoted under
657:ethyl acetoacetate
527:"Electrosynthesis"
252:non-Kolbe reaction
234:Kolbe electrolysis
196:Organic oxidations
65:Experimental setup
57:has potential for
35:chemical compounds
2117:Organic chemistry
2094:
2093:
2007:Peptide synthesis
2002:Organic synthesis
1997:One-pot synthesis
1932:Bioretrosynthesis
1866:10.1149/1.2776733
1825:(28): 6961–6965.
1739:(5393): 313–315.
1713:Collected Volumes
1701:Organic Syntheses
1622:10.1021/cr068357u
1578:(10): 2303–2306.
1370:10.1021/jo0358473
1304:Organic Syntheses
1282:Organic Syntheses
1104:(16): 4149–4155.
997:hydrogen fluoride
588:
587:
580:
562:
477:hydrodimerization
415:propargyl alcohol
403:preparation form
323:coupling reaction
227:Anodic oxidations
216:working electrode
130:at the anode and
2129:
2107:Electrochemistry
2082:
2070:
2069:
2058:
2057:
1992:Mechanosynthesis
1967:Electrosynthesis
1901:
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1878:
1871:
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1684:
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1671:
1665:
1664:
1655:(3): 3187–3191.
1640:
1634:
1633:
1610:Chemical Reviews
1606:Yasuda, Hiroyuki
1594:
1588:
1587:
1567:
1561:
1560:
1532:
1526:
1525:
1516:(3): 3312–3318.
1499:
1493:
1492:
1487:. Archived from
1481:
1475:
1474:
1465:(9): 1213–1226.
1452:
1443:
1442:
1416:
1410:
1409:
1407:
1396:ACS Org Inorg Au
1388:
1382:
1381:
1364:(7): 2423–2426.
1353:
1344:
1343:
1323:
1317:
1316:
1311:. Archived from
1301:
1295:
1294:
1289:. Archived from
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1273:
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1252:
1246:
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1235:
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1201:
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1089:
1083:
1073:
1067:
1066:
1055:10.1039/b512308a
1038:
963:cyanoacetic acid
959:anodic oxidation
944:
935:
934:
931:
917:
907:
905:
904:
901:
880:
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865:
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840:(in the form of
801:
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728:
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596:
583:
576:
572:
569:
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561:
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488:
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382:Cyanoacetic acid
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359:by oxidation of
299:
271:
245:
55:Electrooxidation
27:electrosynthesis
23:electrochemistry
2137:
2136:
2132:
2131:
2130:
2128:
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2126:
2097:
2096:
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2037:Total synthesis
1910:
1905:
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1850:
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1816:
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1135:
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1086:
1074:
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1039:
1035:
1030:
1017:
1005:
989:
983:
951:
949:Redox reactions
943:
939:
932:
929:
928:
926:
922:
916:
912:
911:If the feed is
902:
899:
898:
896:
892:
888:
875:
872:
871:
869:
862:
859:
858:
856:
839:
778:carboxylic acid
763:benzyl chloride
743:is prepared in
655:from alkylated
607:Birch reduction
603:arene compounds
584:
573:
567:
564:
521:
519:
509:
497:
470:
466:
462:
458:
424:
364:
317:Oxidation of a
306:Shono oxidation
229:
220:diffusion layer
193:
153:stainless steel
119:dichloromethane
67:
43:redox reactions
17:
12:
11:
5:
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2017:Retrosynthesis
2014:
2012:Radiosynthesis
2009:
2004:
1999:
1994:
1989:
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1969:
1964:
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1957:Direct process
1954:
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1942:Chemosynthesis
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1790:(2): 227–232.
1774:
1728:
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1666:
1635:
1602:Choi, Jun-Chul
1589:
1562:
1543:(5): 657–659.
1527:
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1411:
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1345:
1334:(5): 921–955.
1318:
1296:
1274:
1263:(2): 145–146.
1247:
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1189:
1160:
1133:
1084:
1068:
1049:(7): 605–621.
1043:Chem. Soc. Rev
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985:Main article:
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897:O + 2e → HCO
882:
881:
870:O + 2e → HCO
853:
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830:
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793:
790:glyoxylic acid
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691:phenethylamine
687:benzyl cyanide
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1234:
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1190:9780444720078
1186:
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1125:
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1027:
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835:
831:
828:
824:
820:
817:
813:
812:cinnamic acid
809:
805:
804:
800:
796:
795:
791:
787:
783:
779:
775:
772:
768:
764:
761:
757:
756:carboxylation
753:
750:
746:
742:
739:
738:
734:
730:
727:
723:
722:
718:
714:
711:can give the
710:
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696:
692:
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681:to a primary
680:
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650:
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642:
641:
637:
633:
632:
631:
629:
621:
617:
616:
612:
611:phthalic acid
608:
604:
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591:
582:
579:
571:
568:February 2022
560:
557:
553:
550:
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539:
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532:
529: –
528:
524:
523:Find sources:
517:
513:
507:
506:
501:This article
499:
495:
490:
489:
486:
485:acrylonitrile
482:
478:
474:
457:
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451:acrylonitrile
448:
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178:
177:polypropylene
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137:
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100:
96:
92:
88:
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80:
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72:
71:galvanic cell
64:
62:
60:
56:
52:
48:
44:
40:
36:
32:
28:
24:
19:
2083:
2071:
2059:
1966:
1937:Biosynthesis
1857:
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1847:
1822:
1818:
1812:
1787:
1783:
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1705:
1699:
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1652:
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1613:
1609:
1592:
1575:
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1565:
1540:
1536:
1530:
1513:
1507:
1497:
1489:the original
1479:
1462:
1456:
1420:
1414:
1395:
1386:
1361:
1357:
1331:
1327:
1321:
1313:the original
1303:
1299:
1291:the original
1281:
1277:
1260:
1256:
1250:
1213:
1209:
1199:
1174:
1146:
1142:
1136:
1101:
1097:
1087:
1079:
1075:
1071:
1046:
1042:
1036:
990:
973:
958:
954:
927:+ OH → HCO
910:
883:
816:electrolysis
749:nitrobenzene
653:hydrocarbons
649:Julius Tafel
647:, named for
625:
574:
565:
555:
548:
541:
534:
522:
510:Please help
505:verification
502:
481:adiponitrile
447:adiponitrile
445:In concept,
390:acetonitrile
356:
309:
305:
288:nucleophiles
283:
251:
212:
201:
194:
181:nitrobenzene
115:acetonitrile
75:potentiostat
68:
26:
20:
18:
842:bicarbonate
806:Originally
782:oxalic acid
709:nitroalkene
628:naphthalene
337:amino acids
260:oxonium ion
87:electrolyte
47:selectivity
2101:Categories
1438:3527306730
1149:(3): 157.
1028:References
851:at pH 8.6:
758:of a para-
745:industrial
741:Azobenzene
538:newspapers
256:heteroatom
81:. Typical
79:electrodes
1860:: 47–52.
1572:Chem. Ber
1257:Synthesis
767:Ibuprofen
693:is shown:
397:oxidation
319:carbanion
223:voltage.
191:Reactions
169:porcelain
145:magnesium
61:as well.
31:synthesis
2061:Category
1839:22684819
1804:98437382
1769:24938351
1761:20075248
1630:17564481
1557:96102382
1398:. 2024.
1378:15049640
1242:32633073
1128:28834012
1063:16791332
1003:See also
786:aldehyde
784:) to an
760:isobutyl
341:nitriles
327:malonate
208:Coulombs
165:sintered
141:platinum
136:graphite
132:hydrogen
77:and two
2073:Commons
1741:Bibcode
1733:Science
1233:7589451
1119:5823775
849:cathode
844:) at a
679:nitrile
552:scholar
427:In the
401:nitrile
357:in-situ
254:when a
149:mercury
99:dioxane
83:solvent
29:is the
2085:Portal
1837:
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547:
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405:amines
280:Amides
128:oxygen
95:Protic
51:yields
37:in an
1987:LASiS
1915:Types
1800:S2CID
1765:S2CID
1681:(PDF)
1553:S2CID
879:+ 2OH
836:of CO
717:amine
713:oxime
683:amine
559:JSTOR
545:books
339:form
329:ester
1835:PMID
1757:PMID
1708:: 42
1626:PMID
1433:ISBN
1374:PMID
1261:1982
1238:PMID
1185:ISBN
1124:PMID
1080:1988
1059:PMID
1022:Link
974:both
906:+ OH
846:lead
643:The
630::
531:news
459:2 CH
347:via
343:and
161:zinc
111:base
107:acid
103:salt
85:and
73:, a
49:and
1862:doi
1827:doi
1792:doi
1749:doi
1737:327
1657:doi
1618:doi
1614:107
1580:doi
1576:124
1545:doi
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1467:doi
1425:doi
1400:doi
1366:doi
1336:doi
1265:doi
1228:PMC
1218:doi
1151:doi
1114:PMC
1106:doi
1051:doi
991:In
936:+ /
893:+ H
884:or
866:+ H
857:HCO
814:by
765:to
689:to
514:by
353:AgO
351:at
183:to
175:or
155:or
117:or
109:or
33:of
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361:Ag
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365:O
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333:α
310:N
284:N
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