Reformatsky reaction: Difference between revisions

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Some reviews have been published.<ref>{{ cite journal | author = Shriner, R. L. | title = The Reformatsky Reaction | journal = Organic Reactions | year = 1942 | volume = 1 | pages = 1–37 | doi = 10.1002/0471264180.or001.01 | isbn = 9780471264187 }}</ref><ref>{{ cite journal | author = Rathke, M. W. | title = The Reformatsky Reaction | journal = Organic Reactions | year = 1975 | volume = 22 | pages = 423–460 | doi = 10.1002/0471264180.or022.04 | isbn = 0471264180 }}</ref>
Some reviews have been published.<ref>{{ cite journal | author = Shriner, R. L. | title = The Reformatsky Reaction | journal = Organic Reactions | year = 1942 | volume = 1 | pages = 1–37 | doi = 10.1002/0471264180.or001.01 | isbn = 9780471264187 }}</ref><ref>{{ cite journal | author = Rathke, M. W. | title = The Reformatsky Reaction | journal = Organic Reactions | year = 1975 | volume = 22 | pages = 423–460 | doi = 10.1002/0471264180.or022.04 | isbn = 0471264180 }}</ref>


In addition<ref name=Kurti /> to aldehydes and ketones, it has also been shown that the Reformatsky enolate is able to react with [[acid chlorides]],<ref>{{cite journal |last1=Sato |first1=Toshio |last2=Itoh |first2=Toshiyuki |last3=Fujisawa |first3=Tamotsu |title=Facile synthesis of β-ketoesters by a coupling reaction of the Reformatsky reagent with acyl chlorides catalyzed by a palladium complex |journal=Chemistry Letters |year=1982 |volume=11 |issue=10 |pages=1559–1560 |doi=10.1246/cl.1982.1559}}</ref>  [[imines]],<ref>{{cite journal |last1=Gilman |first1=Henry |last2=Speeter |first2=Merrill |title=The Reformatsky Reaction with Benzalaniline |journal=[[Journal of the American Chemical Society]] |date=1943 |volume=65 |issue=11 |pages=2255–2256 |doi=10.1021/ja01251a503}}</ref> [[nitriles]] (see [[Blaise reaction]]), and [[nitrones]].<ref>{{cite journal |last1= Stamm |first1=H. |last2=Steudle |first2=H. |title=Nitrone—XI Isoxazolidin-verbindungen—VIII : N-substituierte 5-isoxazolidinone durch reformatzky-reaktion mit nitronen |journal=Tetrahedron |date=1979 |volume=35 |issue=5 |pages=647–650 |doi=10.1016/0040-4020(79)87010-6}}</ref> Moreover,<ref name=Kurti /> metals other than zinc have also been used, including [[magnesium]],<ref>{{cite journal |last1=Moriwake |first1=Tosio |title=The Reformatsky Reaction. I. Condensation of Ketones and t-Butyl Bromoacetate by Magnesium |journal=[[The Journal of Organic Chemistry]] |date=1966 |volume=31 |issue=3 |pages=983–985 |doi=10.1021/jo01341a524}}</ref> [[iron]],<ref name="Iron">{{cite journal |last1=Liu |first1=Xuan-Yu |last2=Li |first2=Xiang-Rui |last3=Zhang |first3=Chen |last4=Chu |first4=Xue-Qiang |last5=Rao |first5=Weidong |last6=Loh |first6=Teck-Peng |last7=Shen |first7=Zhi-Liang |title=Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds |journal=[[Organic Letters]] |date=2019 |volume=21 |issue=15 |pages=5873–5878 |doi=10.1021/acs.orglett.9b01999|pmid=31318222 |s2cid=197541600 }}</ref> [[cobalt]],<ref>{{cite journal |last1=Orsini |first1=Fulvia |last2=Pelizzoni |first2=Francesca |last3=Pulici |first3=Maurizio |last4=Vallarino |first4=Lidia M. |title=A cobalt-phosphine complex as mediator in the formation of carbon-carbon bonds |journal=[[The Journal of Organic Chemistry]] |date=1994 |volume=59 |issue=1 |pages=1–3 |doi=10.1021/jo00080a001}}</ref> [[nickel]],<ref>{{cite journal |last1=Inaba |first1=Shin-ichi |last2=Rieke |first2=Reuben D. |title=Reformatsky type additions of haloacetonitriles to aldehydes mediated by metallic nickel |journal=[[Tetrahedron Letters]] |date=1985 |volume=26 |issue=2 |pages=155–156 |doi=10.1016/S0040-4039(00)61867-1}}</ref> [[germanium]],<ref>{{cite journal |last1=Kagoshima |first1=Hirotaka |last2=Hashimoto |first2=Yukihiko |last3=Oguro |first3=Dai |last4=Saigo |first4=Kazuhiko |title=An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction |journal=[[The Journal of Organic Chemistry]] |date=1998 |volume=63 |issue=3 |pages=691–697 |doi=10.1021/jo971672j|pmid=11672062 }}</ref> [[cadmium]],<ref>{{cite journal |last1=Burkhardt |first1=Elizabeth R. |last2=Rieke |first2=Reuben D. |title=The direct preparation of organocadmium compounds from highly reactive cadmium metal powders |journal=[[The Journal of Organic Chemistry]] |date=1985 |volume=50 |issue=3 |pages=416–417 |doi= 10.1021/jo00203a036}}</ref> [[indium]],<ref>{{cite journal |last1=Chao |first1=Li-Chung |last2=Rieke |first2=Reuben D. |title=Activated metals. IX. New reformatsky reagent involving activated indium for the preparation of β-hydroxy esters |journal=[[The Journal of Organic Chemistry]] |date=1975 |volume=40 |issue=15 |pages=2253–2255 |doi=10.1021/jo00903a031}}</ref><ref>{{cite journal |last1=Araki |first1=Shuki |last2=Ito |first2=Hirokazu |last3=Butsugan |first3=Yasuo |title=Synthesis of β-Hydroxyesters by Reformatsky Reaction Using Indium Metal |journal=Synthetic Communications |date=1988 |volume=18 |issue=4 |pages=453–458 |doi=10.1080/00397918808064009}}</ref> [[barium]],<ref>{{cite journal |last1= Yanagisawa |first1=Akira |last2=Takahashi |first2=Hiroshi |last3=Arai |first3=Takayoshi |title=Reactive barium-promoted Reformatsky-type reaction of α-chloroketones with aldehydes |journal=Chemical Communications |date=2004 |issue=5 |pages=580–581 |doi=10.1039/B314752P|pmid=14973617 }}</ref> and [[cerium]].<ref name="cerium">{{cite journal |last1=Imamoto |first1=Tsuneo |last2=Kusumoto |first2=Tetsuo |last3=Tawarayama |first3=Yoshinori |last4=Sugiura |first4=Yasushi |last5=Mita |first5=Takeshi |last6=Hatanaka |first6=Yasuo |last7=Yokoyama |first7=Masataka |title=Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents |journal=[[The Journal of Organic Chemistry]] |date=1984 |volume=49 |issue=21 |pages=3904–3912 |doi=10.1021/jo00195a006}}</ref> Additionally,<ref name=Kurti /> metal salts are also applicable in place of metals, notably [[samarium(II) iodide]],<ref>{{cite journal |last1=Tabuchi |first1=Takanori |last2=Kawamura |first2=Kisa |last3=Inanaga |first3=Junji |last4=Yamaguchi |first4=Masaru |title=Preparation of medium- and large-ring lactones. SmI2-induced cyclization of ω-(α-bromoacyloxy) aldehydes |journal=[[Tetrahedron Letters]] |date=1986 |volume=27 |issue=33 |pages=3889–3890 |doi=10.1016/S0040-4039(00)83907-6}}</ref><ref>{{cite journal |last1=Molander |first1=Gary A. |last2=Etter |first2=Jeffrey B. |title=Lanthanides in organic synthesis. 8. 1.3-Asymmetric induction in intramolecular Reformatskii-type reactions promoted by samarium diiodide |journal=[[Journal of the American Chemical Society]] |date=1987 |volume=109 |issue=21 |pages=6556–6558 |doi=10.1021/ja00255a076}}</ref> [[chromium(II) chloride]],<ref>{{cite journal |last1=Dubois |first1=Jacques-Emile |last2=Axiotis |first2=Georges |last3=Bertounesque |first3=Emmanuel |title=Chromium (II) chloride : a new reagent for cross-aldol reactions |journal=[[Tetrahedron Letters]] |date=1985 |volume=26 |issue=36 |pages=4371–4372 |doi=10.1016/S0040-4039(00)98737-9}}</ref> [[titanium(II) chloride]],<ref>{{cite journal |last1=Ishihara |first1=Takashi |last2=Yamanaka |first2=Tohru |last3=Ando |first3=Teiichi |title=New low-valent titanium catalyzed reaction of chlorodifluoromethyl ketones leading to α,α-difluorinated β-hydroxy ketones |journal=[[Chemistry Letters]] |date=1984 |volume=13 |issue=7 |pages=1165–1168 |doi=10.1246/cl.1984.1165}}</ref> cerium(III) halides such as [[cerium(III) iodide]],<ref>{{cite journal |last1=Fukuzawa |first1=Shin-Ichi |last2=Fujinami |first2=Tatsuo |last3=Sakai |first3=Shizuyoshi |title=Carbon–carbon bond formation between α-halogenoketones and aldehydes promoted by cerium(III) iodide or cerium(III) chloride–sodium iodide |journal=Journal of the Chemical Society, Chemical Communications |date=1985 |issue=12 |pages=777–778 |doi=10.1039/C39850000777}}</ref> and [[Bis(cyclopentadienyl)titanium(III) chloride|titanocene(III) chloride]].<ref>{{cite journal |last1=Parrish |first1=J. D. |last2=Shelton |first2=Daniel R. |last3=Little |first3=R. Daniel |title=Titanocene(III)-Promoted Reformatsky Additions |journal=[[Organic Letters]] |date=2003 |volume=5 |issue=20 |pages=3615–3617 |doi=10.1021/ol035269c|pmid=14507186 }}</ref>
In addition<ref name=Kurti /> to aldehydes and ketones, it has also been shown that the Reformatsky enolate is able to react with [[acid chlorides]],<ref>{{cite journal |last1=Sato |first1=Toshio |last2=Itoh |first2=Toshiyuki |last3=Fujisawa |first3=Tamotsu |title=Facile synthesis of β-ketoesters by a coupling reaction of the Reformatsky reagent with acyl chlorides catalyzed by a palladium complex |journal=Chemistry Letters |year=1982 |volume=11 |issue=10 |pages=1559–1560 |doi=10.1246/cl.1982.1559}}</ref>  [[imines]],<ref>{{cite journal |last1=Gilman |first1=Henry |last2=Speeter |first2=Merrill |title=The Reformatsky Reaction with Benzalaniline |journal=[[Journal of the American Chemical Society]] |date=1943 |volume=65 |issue=11 |pages=2255–2256 |doi=10.1021/ja01251a503|bibcode=1943JAChS..65.2255G }}</ref> [[nitriles]] (see [[Blaise reaction]]), and [[nitrones]].<ref>{{cite journal |last1= Stamm |first1=H. |last2=Steudle |first2=H. |title=Nitrone—XI Isoxazolidin-verbindungen—VIII : N-substituierte 5-isoxazolidinone durch reformatzky-reaktion mit nitronen |journal=Tetrahedron |date=1979 |volume=35 |issue=5 |pages=647–650 |doi=10.1016/0040-4020(79)87010-6}}</ref> Moreover,<ref name=Kurti /> metals other than zinc have also been used, including [[magnesium]],<ref>{{cite journal |last1=Moriwake |first1=Tosio |title=The Reformatsky Reaction. I. Condensation of Ketones and t-Butyl Bromoacetate by Magnesium |journal=[[The Journal of Organic Chemistry]] |date=1966 |volume=31 |issue=3 |pages=983–985 |doi=10.1021/jo01341a524}}</ref> [[iron]],<ref name="Iron">{{cite journal |last1=Liu |first1=Xuan-Yu |last2=Li |first2=Xiang-Rui |last3=Zhang |first3=Chen |last4=Chu |first4=Xue-Qiang |last5=Rao |first5=Weidong |last6=Loh |first6=Teck-Peng |last7=Shen |first7=Zhi-Liang |title=Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds |journal=[[Organic Letters]] |date=2019 |volume=21 |issue=15 |pages=5873–5878 |doi=10.1021/acs.orglett.9b01999|pmid=31318222 |s2cid=197541600 }}</ref> [[cobalt]],<ref>{{cite journal |last1=Orsini |first1=Fulvia |last2=Pelizzoni |first2=Francesca |last3=Pulici |first3=Maurizio |last4=Vallarino |first4=Lidia M. |title=A cobalt-phosphine complex as mediator in the formation of carbon-carbon bonds |journal=[[The Journal of Organic Chemistry]] |date=1994 |volume=59 |issue=1 |pages=1–3 |doi=10.1021/jo00080a001}}</ref> [[nickel]],<ref>{{cite journal |last1=Inaba |first1=Shin-ichi |last2=Rieke |first2=Reuben D. |title=Reformatsky type additions of haloacetonitriles to aldehydes mediated by metallic nickel |journal=[[Tetrahedron Letters]] |date=1985 |volume=26 |issue=2 |pages=155–156 |doi=10.1016/S0040-4039(00)61867-1}}</ref> [[germanium]],<ref>{{cite journal |last1=Kagoshima |first1=Hirotaka |last2=Hashimoto |first2=Yukihiko |last3=Oguro |first3=Dai |last4=Saigo |first4=Kazuhiko |title=An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction |journal=[[The Journal of Organic Chemistry]] |date=1998 |volume=63 |issue=3 |pages=691–697 |doi=10.1021/jo971672j|pmid=11672062 }}</ref> [[cadmium]],<ref>{{cite journal |last1=Burkhardt |first1=Elizabeth R. |last2=Rieke |first2=Reuben D. |title=The direct preparation of organocadmium compounds from highly reactive cadmium metal powders |journal=[[The Journal of Organic Chemistry]] |date=1985 |volume=50 |issue=3 |pages=416–417 |doi= 10.1021/jo00203a036}}</ref> [[indium]],<ref>{{cite journal |last1=Chao |first1=Li-Chung |last2=Rieke |first2=Reuben D. |title=Activated metals. IX. New reformatsky reagent involving activated indium for the preparation of β-hydroxy esters |journal=[[The Journal of Organic Chemistry]] |date=1975 |volume=40 |issue=15 |pages=2253–2255 |doi=10.1021/jo00903a031}}</ref><ref>{{cite journal |last1=Araki |first1=Shuki |last2=Ito |first2=Hirokazu |last3=Butsugan |first3=Yasuo |title=Synthesis of β-Hydroxyesters by Reformatsky Reaction Using Indium Metal |journal=Synthetic Communications |date=1988 |volume=18 |issue=4 |pages=453–458 |doi=10.1080/00397918808064009}}</ref> [[barium]],<ref>{{cite journal |last1= Yanagisawa |first1=Akira |last2=Takahashi |first2=Hiroshi |last3=Arai |first3=Takayoshi |title=Reactive barium-promoted Reformatsky-type reaction of α-chloroketones with aldehydes |journal=Chemical Communications |date=2004 |issue=5 |pages=580–581 |doi=10.1039/B314752P|pmid=14973617 }}</ref> and [[cerium]].<ref name="cerium">{{cite journal |last1=Imamoto |first1=Tsuneo |last2=Kusumoto |first2=Tetsuo |last3=Tawarayama |first3=Yoshinori |last4=Sugiura |first4=Yasushi |last5=Mita |first5=Takeshi |last6=Hatanaka |first6=Yasuo |last7=Yokoyama |first7=Masataka |title=Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents |journal=[[The Journal of Organic Chemistry]] |date=1984 |volume=49 |issue=21 |pages=3904–3912 |doi=10.1021/jo00195a006}}</ref> Additionally,<ref name=Kurti /> metal salts are also applicable in place of metals, notably [[samarium(II) iodide]],<ref>{{cite journal |last1=Tabuchi |first1=Takanori |last2=Kawamura |first2=Kisa |last3=Inanaga |first3=Junji |last4=Yamaguchi |first4=Masaru |title=Preparation of medium- and large-ring lactones. SmI2-induced cyclization of ω-(α-bromoacyloxy) aldehydes |journal=[[Tetrahedron Letters]] |date=1986 |volume=27 |issue=33 |pages=3889–3890 |doi=10.1016/S0040-4039(00)83907-6}}</ref><ref>{{cite journal |last1=Molander |first1=Gary A. |last2=Etter |first2=Jeffrey B. |title=Lanthanides in organic synthesis. 8. 1.3-Asymmetric induction in intramolecular Reformatskii-type reactions promoted by samarium diiodide |journal=[[Journal of the American Chemical Society]] |date=1987 |volume=109 |issue=21 |pages=6556–6558 |doi=10.1021/ja00255a076|bibcode=1987JAChS.109.6556M }}</ref> [[chromium(II) chloride]],<ref>{{cite journal |last1=Dubois |first1=Jacques-Emile |last2=Axiotis |first2=Georges |last3=Bertounesque |first3=Emmanuel |title=Chromium (II) chloride : a new reagent for cross-aldol reactions |journal=[[Tetrahedron Letters]] |date=1985 |volume=26 |issue=36 |pages=4371–4372 |doi=10.1016/S0040-4039(00)98737-9}}</ref> [[titanium(II) chloride]],<ref>{{cite journal |last1=Ishihara |first1=Takashi |last2=Yamanaka |first2=Tohru |last3=Ando |first3=Teiichi |title=New low-valent titanium catalyzed reaction of chlorodifluoromethyl ketones leading to α,α-difluorinated β-hydroxy ketones |journal=[[Chemistry Letters]] |date=1984 |volume=13 |issue=7 |pages=1165–1168 |doi=10.1246/cl.1984.1165}}</ref> cerium(III) halides such as [[cerium(III) iodide]],<ref>{{cite journal |last1=Fukuzawa |first1=Shin-Ichi |last2=Fujinami |first2=Tatsuo |last3=Sakai |first3=Shizuyoshi |title=Carbon–carbon bond formation between α-halogenoketones and aldehydes promoted by cerium(III) iodide or cerium(III) chloride–sodium iodide |journal=Journal of the Chemical Society, Chemical Communications |date=1985 |issue=12 |pages=777–778 |doi=10.1039/C39850000777}}</ref> and [[Bis(cyclopentadienyl)titanium(III) chloride|titanocene(III) chloride]].<ref>{{cite journal |last1=Parrish |first1=J. D. |last2=Shelton |first2=Daniel R. |last3=Little |first3=R. Daniel |title=Titanocene(III)-Promoted Reformatsky Additions |journal=[[Organic Letters]] |date=2003 |volume=5 |issue=20 |pages=3615–3617 |doi=10.1021/ol035269c|pmid=14507186 }}</ref>


== Structure of the reagent ==
== Structure of the reagent ==
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== Variations ==
== Variations ==
In one variation of the Reformatsky reaction<ref name="Lambert">{{cite journal |author1=Lambert, T. H. |author2=Danishefsky, S. J. | title = Total Synthesis of UCS1025A | journal = [[Journal of the American Chemical Society]] | year = 2006 | volume = 128 | issue = 2 | pages = 426–427 | doi = 10.1021/ja0574567 |pmid=16402826}}</ref> an [[lactam|iodolactam]] is coupled with an [[aldehyde]] with [[triethylborane]] in [[toluene]] at −78&nbsp;°C.
In one variation of the Reformatsky reaction<ref name="Lambert">{{cite journal |author1=Lambert, T. H. |author2=Danishefsky, S. J. | title = Total Synthesis of UCS1025A | journal = [[Journal of the American Chemical Society]] | year = 2006 | volume = 128 | issue = 2 | pages = 426–427 | doi = 10.1021/ja0574567 |pmid=16402826|bibcode=2006JAChS.128..426L }}</ref> an [[lactam|iodolactam]] is coupled with an [[aldehyde]] with [[triethylborane]] in [[toluene]] at −78&nbsp;°C.


[[Image:Reformatskii Danishefsky 2006.png|center|400px|Reformatsky reaction Danishefsky variation<ref name="Lambert"/>]]
[[Image:Reformatskii Danishefsky 2006.png|center|400px|Reformatsky reaction Danishefsky variation<ref name="Lambert"/>]]

Latest revision as of 12:50, 24 June 2025

Template:Short description Template:Reactionbox

The Reformatsky reaction (sometimes transliterated as Reformatskii reaction) is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:[1][2]

The Reformatsky reaction
The Reformatsky reaction

The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatsky enolates are less reactive than lithium enolates or Grignard reagents and hence nucleophilic addition to the ester group does not occur. The reaction was discovered by Sergey Nikolaevich Reformatsky.

Some reviews have been published.[3][4]

In addition[5] to aldehydes and ketones, it has also been shown that the Reformatsky enolate is able to react with acid chlorides,[6] imines,[7] nitriles (see Blaise reaction), and nitrones.[8] Moreover,[5] metals other than zinc have also been used, including magnesium,[9] iron,[10] cobalt,[11] nickel,[12] germanium,[13] cadmium,[14] indium,[15][16] barium,[17] and cerium.[18] Additionally,[5] metal salts are also applicable in place of metals, notably samarium(II) iodide,[19][20] chromium(II) chloride,[21] titanium(II) chloride,[22] cerium(III) halides such as cerium(III) iodide,[23] and titanocene(III) chloride.[24]

Structure of the reagent

The crystal structures of the THF complexes of the Reformatsky reagents tert-butyl bromozincacetate[25] and ethyl bromozincacetate[26] have been determined. Both form cyclic eight-membered dimers in the solid state, but differ in stereochemistry: the eight-membered ring in the ethyl derivative adopts a tub-shaped conformation and has cis bromo groups and cis THF ligands, whereas in the tert-butyl derivative, the ring is in a chair form and the bromo groups and THF ligands are trans. Note that, in contrast to lithium and boron enolates, which have the metal(loid)s exclusively bond to oxygen, the zinc enolate moiety in the Reformatsky reagents have zinc atoms that are simultaneously O- and C-bound and can therefore be described as "organometallic".

File:Ethyl-bromozincacetate-from-xtal-3D-sticks-C.png
File:Ethyl-bromozincacetate-THF-dimer-from-xtal-2D-skeletal-D.png		 File:Tert-butyl-bromozincacetate-from-xtal-3D-sticks-C.png
File:Tert-butyl-bromozincacetate-THF-dimer-from-xtal-2D-skeletal-D.png
ethyl bromozincacetate dimer tert-butyl bromozincacetate dimer

Reaction mechanism

Zinc metal is inserted into the carbon-halogen bond of the α-haloester by oxidative addition 1. This compound dimerizes and rearranges to form two zinc enolates 2. The oxygen on an aldehyde or ketone coordinates to the zinc to form the six-member chair like transition state 3. A rearrangement occurs in which zinc switches to the aldehyde or ketone oxygen and a carbon-carbon bond is formed 4. Acid workup 5,6 removes zinc to yield zinc(II) salts and a β-hydroxy-ester 7.[5]

File:RefRxn3.svg

Variations

In one variation of the Reformatsky reaction[27] an iodolactam is coupled with an aldehyde with triethylborane in toluene at −78 °C.

Reformatsky reaction Danishefsky variation[27]
Reformatsky reaction Danishefsky variation[27]

See also

References

Template:Reflist

  1. ↑ Script error: No such module "Citation/CS1".
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ Script error: No such module "Citation/CS1".
  5. ↑ a b c d Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Burlington, 2005.
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Script error: No such module "Citation/CS1".
  17. ↑ Script error: No such module "Citation/CS1".
  18. ↑ Script error: No such module "Citation/CS1".
  19. ↑ Script error: No such module "Citation/CS1".
  20. ↑ Script error: No such module "Citation/CS1".
  21. ↑ Script error: No such module "Citation/CS1".
  22. ↑ Script error: No such module "Citation/CS1".
  23. ↑ Script error: No such module "Citation/CS1".
  24. ↑ Script error: No such module "Citation/CS1".
  25. ↑ Script error: No such module "Citation/CS1".
  26. ↑ Script error: No such module "Citation/CS1".
  27. ↑ a b Script error: No such module "Citation/CS1".
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