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Synthetic Communications: An
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Organic Chemistry
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1,3-
Di(Ferrocenylmethyl)Imidazolium
and 1-Ferrocenylmethyl-3-
Alkylimidazolium Salts: A High
Yield and Facile Synthesis
J. Howarth
a
, J-L. Thomas
a
, K. Hanlon
a
& D.
McGuirk
a
a
School of Chemical Sciences, Dublin City
University , Dublin, 9, Ireland
Published online: 04 Dec 2007.
To cite this article: J. Howarth , J-L. Thomas , K. Hanlon & D. McGuirk (2000) 1,3-
Di(Ferrocenylmethyl)Imidazolium and 1-Ferrocenylmethyl-3-Alkylimidazolium Salts: A
High Yield and Facile Synthesis, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 30:10, 1865-1878, DOI:
10.1080/00397910008087232
To link to this article: http://dx.doi.org/10.1080/00397910008087232
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3. SYNTHETICCOMMUNICATIONS,30(10), 1865-1878 (2000)
1,3-DI(FEXROCENnMETHYL)IMIDAZOLIUMAND
l-FERROCENYLMETHYL-3KYLIMIDAZOLIUMSALTS: A HIGH
YIELDAND FACILESYNTHESLS
J. Howarth,*J-L.Thomas,K. Hanlon and D. McGuirk
Schoolof ChemicalSciences,DublinCityUniversity, Dublin 9. Ireland
ABSTRACT We have developed a rapid facile synthesis of 1-femnyl-3-alkyl
and 1,3-di(ferrocenylmethyl)imidazolium salts. The imidazoliumsalts are formed
in excellentyields.
Interest in 13-substituted imidazolium salts ranges from their use as
solventsin the form of ionicliquids' to precursorsfor the imidazoline-2-ylidenes?
both of these areas are now well documented. We have an interest in these
systems as Lewis acid catalysts3and as backbone structures for anion re~eptors.~
In particular we have investigated 1-ferrocenylmethyl-3-alkyl and 1.3-
di(ferrocenylmethy1)imidazolium salts and we report here new rapid and facile
synthesesof suchsystems,in which good to excellentyieldsare obtained.
* To whom correspondenceshould be addressed
1865
Copyright Q 2000 by Marcel Dekker, Inc. www.dekker.com
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4. 1866 HOWARTH ETAL.
The general syntheses for the ferrocenylmethylimidazole derivatives are
outlined in Scheme 1. We found that we could produce the three
femcenylmethylimidazolederivatives, 2.3,6 and 9 from the intermediate
(ferrocenylmethy1)tethylammoniurn iodide salt 1, which was prepared
according to the Monoferrocenylmethyl substituted
imidazolium iodidesalts 6a-e (Table 1)were prepared simplyby heatingN-
akyl substituted imidazolesin dry acetonitrileunder reflux with 1. The N-
akyl substitutedimidazoles5 were formed according to B6nhote et al?, or
obtained from Aldrich Chemical Co. The 1,3-di(ferrocenylmethyl)-
imidazoliumiodide3 (Table 1) was formed in 80% yield from a 1:1mixture
of 1and 2 in dry acetonitrileheated under reflux for 18 h. Compound3can
also be formed in 69% yield by heating 1 in dry acetonitrile with two
equivalentsof imidazole,in the presence of sodium carbonate, at reflux for
one week. l-Fem>cenylmethylirnidazole2was produced from the reaction
of imidazole sodium salt*with 1in acetonitrileheated under reflux for 24h.
Alternatively, 2 can be formed from ferroceny~methylarni~~~using the
conditions given by Arduengo et al." These mutes to 2 and 3 represent a
significant improvement over the current literature protocols.8
l-Ferrocenylmethylimidazole derivatives 9a-c (Table 2) were prepared by
the reaction of 1 equivalentof 1with the appropriate substituted imidazole
system 8, which are available from Aldrich Chemical Co. Unfortunately,
further Veatment of compounds9a-c with a secondequivalent of 1failed to
give the corresponding 1.3-difemnylmethyl iodidesalts.
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5. IMIDAZOLIUMSALTS 1867
MeCN
A -N=N
I- Fe
N,,NNa G D 2
6X =I, 7 X =PF
6b, 7b R =Et, R' =R2=H
6 ~ ,7~R =Pr,R' =R2=€I
6% 7a R =Me, Rp= Rz=H
6d,7d R =Et, R' =Me, R2= (31
6e,7e R =Bu, R' =R2=H
R'
WRMeCNA -N-N
1 -Fe
9a R =R' =CI, R2=H
9b R =R' =CN, R2=H
9c R =H, R'= N02,R2=Me
R+(R' ea
Scheme1
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6. 1868 HOWARTHET AL.
Ferrocenylmethylimidoliurn iodides 3 and 6a-e were characterised by
elemental analysis performed on their hexafluorophosphate derivatives 4
and 7ae. The latter were prepad in almost quantitative yield by treatment
of the iodide saltswith "f%PFa in acetone at room temperature.
Entry
3.
6a
6b
6c
6d
6 2
Table 1:l-Femcenylmethyl-3-allryl-and 1.3-fenocenylmethylimidazolium
R, R', Rz Yield (%)
R =FcCHZ-,R' =Rz =H 68,80*
R =Me, R' =R2= H 71
R = E ~ , R ' = ' R ~ = H 67
R = P ~ , R '= R ~ = H 68
R=Et,R'=Me,R2=C1 83
82R =BU,R' =R~=H
Entry
2
9a
9b
9c
I I I
*Fc = F e m n y l , compound 3was prepared by two different
R, R', RZ Yield (%)
51,69,83*
83
R =R' =R~=H
.R =R' =a,R~=H
R = R ' = C N , R ~ = H 74
R =H,R' =N& Rz =Me 97
Table 2: 1-Ferrocenylmethylirnidazolederivatives.
DUteS.
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7. IMIDAZOLIUMSALTS 1869
EXPERIMENTAL
Elemental analyses were performed by the Microanalytical Laboratory of
University College Dublin, Ireland FT NMR spectra were recorded using a
Bruker ACS 400MHz spectrometer. Diethyl ether was dried over sodium,and
MeCN and ethanol with 4A molecular sieves. 4,5-DicNoroimidazole, 2-methyl-
5-nitroimidazole, 4,5-dicyanoimidazole,l-methylimidazole and 1-butylimidazole
were obtainedfrom Aldrich ChemicalsCo and usedwithoutfurther purification.
General procedure for the preparation of l-ferrocenylmethyllmidazole
derivatives.
A solution of (ferrocenylmethy1)trimethylammonium iodide 1 (5.03 g, 13.00
mmol). the appropriate imidazole derivative 8 (14.28 mmol) and potassium
carbonate(2.69 g, 19.47 mmol)in anhydrousMeCN (100ml) was refluxed for 24
h. The cooled solution was poured into water (100 ml) and extracted with
chloroform (3 x 75 ml). The extracts were washed with water (2 x 50 ml), dried
(MgS04)and evaporated to give an orange which slowly solidified after addition
of diethyl ether and few drops of methanol. Filtration of the solution gave an
orangesolidwhichwas washed twice with cold methanolto yield orangecrystals
The followingcompoundswere preparedin the abovemanner.
l-Fe~nylmethyl-4,J-dichloroimidazole.9a (83%),m.p. 90-92 "C. 'H NMR
(cDcl3): 6 3.73 (s, 5H, Cp H), 4.22 (4 J = 2.0 Hz, 2H, Cp H), 4.26 (t, J =2.0 Hz,
2H, Cp H),4.81 (s, 2H, Fc-CHz-), 7.28 (s, lH, 2-Im H). 13CNMR (CDc13):6
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8. 1870 HOWARTH ETAL.
46.41 (Fc-CH~-),69.28-69.55 (Cp C-H and Cp CC), 80.95 (2-h C), 126.29 (4-
Found: C, 50.36; H, 3.66; N, 8.17; C1,Im C-Cl), 134.08 (5-ImC-Cl). Anal.
21.39. Calcd forClJIl~N2C12Fe:C, 50.19; H, 3.61; N, 8.36; C1.21.16.
l-Ferrocenylmethyl4,5-dlcyanolmidazole9b (74%), m.p. 116-118 OC. 'H
NMR (CDCl3): 64.20 (s, 5H, Cp H), 4.26 (t, J = 1.5 Hz,2H, Cp H), 4.30 (t, J =
1.5 Hz, 2H, Cp H), 5.02 (s, 2H, Fc-CH2-X 7.55 (s. 1A. 2-Im H).
(cDCI3): 6 47.69 (Fc-CHZ-),68.64-69.49 (Cp C-H and Cp C-C),78.17 (2-Im C),
13C NMR
107.72 (CN), 111.14 (CN), 122.51 (4-Im C-CN), 139.95 (5-ImC-CN). Anal.
Found: C, 60.55; H, 3.84; N, 17.55. Calcd for ClaH12N.pe: C, 60.79; H, 3.83; N,
17.72.
l-F~nylmethyl-2methyl-5-nitroimidazoe!k (97%),mp. 162-164OC. 'H
NMR (CDC13): 6 2.46 (s, 3H, CH3),4.21-4.23 (m, 7H, Cp H),4.27 (t,J = 2.0 Hz,
2H, Cp H), 4.81 (s,2H, Fc-CHZ-). 13CNMR (CDC13): 6 13.33 (CH3). 47.08 (FC-
CHz-), 68.87-69.51 (Cp C-Hand Cp C-C), 79.88 (2-Im C), 119.24 (5-Im C),
143.97 (C-NO& Anal. Found C, 55.32; H, 4.65; N. 12.75. Calcd for
CISH~SN~OZF~:C, 55.41; H, 4.65; N, 12.92.
l-Ferrocenylmethylimldazole2
Method A: As described above, but in thiscase 1.1.1-Uichloroethane was added
to the orange oil and l ~ - d i ( f e r r o c e n y l ~ ~ y l ~ ~ d ~ ~ ~iodide12 3
precipitated as a yellow solid (0.65 g) which was collected by fdtrationand dried
at mom temperature,'H NMR ( ~ ~ 1 3 ) :64.22 (s, 14H. c p HI,4.44 (s,4 ~ .cp
H), 5.31 (s,4H, Fc-CHZ-),7.17 (s,2H, 4-hH and 5-Im H), 9.92 (s,lH, 2-Im H).
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9. IMIDAZOLIUM SALTS 1871
I3CNMR (cDc13):649.85 (Fc-CHz-), 68.75-69.66 (Cp C-Hand Cp C-C), 120.82
(Im C), 134.66 (2-Im C). 1,l.l-Trichloroethane was evaporated to afford 1-
ferrocenylmethyUmidazole'2 2 as a yellow fine solid (1.74 g, 51%). 'H N M R
(CDC13):64.15-4.18 (m, 9H, Cp H), 4.84 (s, 2H, Fc-CHz-),6.89 (s, lH, 5-ImH).
7.00 (s,lH, 4-ImH),7.46 (s,lH, 2-Im H). I3CNMR (Cmb): 6 46.59 O;C-CH~-).
68.40-68.66 (Cp C-H and Cp C-C),82.49 (2-Im C), 118:95 (4-hC), 136.48 (5-
Im C).
Method B: A solution of (ferrocenylmethyl)trimethylammoniumiodide1(3.05g,
7.79 mmolj itid imidazole sodium salt (0.77 g, 8.57 mmol) in anhydrous MeCN
(75 ml) was ~fluxedfor 24 h. The cooled solution was poured into water (100
ml) and extracted with chloroform (3 x 75 ml). The extracts were washed with
water (2 x 50 ml), dried (MgS04) and evaporated to give an orange oil which
slowly solidifiedto afford 1-ferrocenylmethylimidazole2 as a yellow solid (1.43
g, yield: 69%).identicalin all respectsto that obtained in Method A.
Method C: A solution of ferrocenylmethylamine(2.10 g. 9.3 mmol) and aqueous
ammonia (35%)(0.46 ml, 9.30 mmol) in propanol (50 ml) was added to a sdmd
solution of aqueous glyoxal (40%) (1.17 ml, 10.22 mmol) and aqueous
formaldehyde (37%) (0.77 ml, 10.22 mmol) in propanol (50 ml). The resulting
solutionwas stirred under reflux for 1h. Water (100 ml) was then added and the
aqueous solution was extracted with dichloromethane (3 x 50 ml). The extracts
were washed with water (2 x 50 ml). dried (MgS04)and evaporated to afford an
orange oil which slowly solidifiedto afford l-ferrocenylmethylimdazole2 as a
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10. 1872 HOWARTHET AL..
yellow solid (2.05 g, yield: 83%). identical in all respects to that obtained in
MethodsA and B.
General method for the preparation of 1-Ferrocenylmethylimidazolium
Iodides.
A solution of (ferrocenylmethy1)trimethylammoNumiodide 1 (5.12 g,
13.00 mmol)and the appropriate 1-substitutedimidazolederivative (13.60 mmol)
in anhydrous MeCN (100 ml) was refluxed for 18 h. The cooled solution was
poured into water (75 ml) and extracted with chloroform (3 x 50 ml). The
extracts were washed with water (2 x 50 ml), dried (MgS04) and evaporated to
give an orange oil. Diethyl ether (50 rnl) was then added and the desired salts
precipitated on scratching. The yellow solid was collected by filtration, washed
with diethyletherand dried at room temperature.
The followingcompoundswereprepared in the abovemanner.
l-Ferrocenylmethyl-3-methyUmidazolium iodide" 6s (71%) from 1-
methylimidazole.'H NMR (CDCb):64.02 (s.3H, CH3). 4.23 (s,7H, Cp H), 4.49
(s,2H, Cp H), 5.36 (s,2H. R-CHz-), 7.41 (s, lH,5-Im H), 7.47 (s, lH, 4-Im H).
9.72 (s, lH, 2-hiH). 13C NMR (CDCl3): 6 36.57 (NCH3). 49.34 (Fc-CHZ-),
69.09-69.28 (Cp C-H and Cp C-C), 121.27 (4-h C),123.0 (5-hC),135.11 (2-
Im C).
l-Ferrocenylmethyl-3-ethylimidazolium iodide 6b (67%) from 1ethyl-
imidazole, rn.p. 60-62 OC, 'HNMR (CDCb): 61.57 (t, J =7.4 Hz, 3H, CH2CH3).
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12. 1874 HOWARTH ETAL.
CH2CH2CH2CH3), 1.27 (m, 2H, CH2CH2CH2CHA 1.80 (m, 2H,
CH2CH2CH2CH3),4.18-4.22 (m, 9H, Cp H and CH~CHZCH~CH~),4.45 (t. .I=1.5
Hz, 2H, Cp H), 5.33 (s,2H, Fc-CH~-),7.35 (s, 2H, 4-Im H and 5-Im H), 9.86 (s,
IH, 2-Im H). I3C NMR (cDc.13):6 12.97 (NCH~CHZCH~CH~),18.81
(NCHZCH~CH~CH~),31.48 (NCHZCH~CH~CH~),46.59 (NCH~CH~CHZCH~).
49.03 (FC-CHZ-).68.62-71.77(Cp C-H and Cp C-C), 121.34(4-IIIIC), 121.64(5-
h C), 134.51 (2-Im C).
1~3-di(Ferrocenylmethyl)imidazoliumIodide 3
Method A: As described above (8096), from l-ferrocenylmethyl imidazole 2,
identical in all respectsto that obtained earlier.
Method B: A solution of (ferrocenylmethy1)trimethylammoniumiodide 1 (5.13g,
13.00 mmol), imidazole (0.45 g, 6.50 mmol) and potassium carbonate (1.34 g,
9.70 mmol) in anhydrous MeCN (100 ml) was refluxed for one week. The cooled
solution was poured into water (100 ml) and extracted with chloroform (3 x 75
ml). The extracts were washed with water (2 x 50 ml), dried (MgS04) and
evaporated to give an orange oil. Diethyl ether was added and 1,3-
di(ferroceny1methyl)imidmliumiodide3 precipitatedasa yellow solid (2.60g,
yield: 68%) which was collected by filtration and dried at room temperature,
identical in allrespects to that obtained earlier.
General procedure for the preparation of ferrocenylimidazoliumhexafluoro
phosphates.
Ammonium hexafluorophosphate (5.00mmol) was added in one portion to
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13. IMIDAZOLIUMSALTS 1875
a solutionof the appropriatefemenylimidazolium iodide(5.00 mmol) in acetone
(100 ml) and the reaction mixture was stirred at room temprature for 24 h. The
solutionwas poured intowater (150ml) and the aqueous phase was extractedwith
dichloromethane(3 x 50 ml). The extracts were washed*withwater (2 x 50 ml).
dried (MgS04) and evaporated to yield the femnylimidazolium
hexafluorophosphateasa fine orangesolid.
The followingcompoundswere prepared in the abovemanner.
l-Ferrocenylmethyl-3-methylimidazolium hexafluorophosphate 7a (87%).
m.p. 134-135OC, 'H N M R (ds-Acetone):6 (s,3H, CH3), (s, 7H, Cp H), (s,2H.
Cp H), (s,2H, Fc-CHz-), (s, lH, 5-Im H), (s,lH, 4-Im H). (s,lH, 2-Im H). I3C
NMR (dg-Acetone): 6 (NCH3), (Fc-CHZ-),(Cp C-H and Cp C-C), (4-lm C), (5-
Im C). (2-Im C). Anal. Found: C, 42.08; H. 4.08; N, 6.22. Calcd lor
C I ~ H I ~ N ~ F ~ P F ~ :C. 42.28; H, 4.02; N, 6.57.
l-Ferrocenylmethyl-3-ethylimidazoliumhexafluorophosphate 7b (90%). m.p
119-120OC,'H NMR (cDCl3): 6 (t, J = 7.4 Hz, 3H, CHZCH~),(s,7H, Cp H).
(q, J = 7.4 Hz, 2H. CHZ-CH~),(t,J = 1.5 Hz, 2H, Cp H), (s,2H, Fc-CH~-),
lH, 5-Im H),
(s,
I3C NMR (cDcl3): 6 14.60(s, lH, 4-Im H), (s, lH, 2 - h H).
(NCH2a3). 44.58 (NmZCH3). 49.33 (Fc-CH2-l 68.90-69.39 (Cp C-H and Cp
C-C), 121.11 (4-Im C), 121.25 (5-Im C), 133.78 (2-Im C). Anal. Found: C,
43.42; H. 4.25; N, 6.17. Calcd forC I ~ H I ~ N Z F ~ P F ~ :C, 43.66; H, 4.35; N, 6.36.
l-Fe~nylmethyl-3propylimidazoliumhexatluorophosphate 7c (92%),
m.p. 94-95 "C, 'H N M R (CDC13): 6 0.93 (4J = 7.4 Hz, 3H, CH~CHZCH~),1.88
(m, 2H, CH2CH2CH3),4.07 (t, J = 7.4 Hz, 2H, CH2CH2CH3), 4.24-4.26 (m. 7H,
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14. 1876 HOWARTH ET AL.
Cp H), 4.40 (t, J = 1.5 Hz, 2H. Cp H), 5.18 (s,2H, Fc-CHz-), 7.22 (s,2H, 4-ImH
and 5-ImH), 8.51 (s, lH, 2-Im H). I3CNMR (cDC13): 8 10.06 (NCH~CHZCH~),
22.96 (NCHZCH~CH~),49.17 (Nm2C&CH3), 51.24 (Fc-CH~-),69.03-69.38 (Cp
C-H and Cp C-C), 121.38 (4-Im C), 121.62.(5-Im C), 133.76 (2-Im C). Anal.
Found C, 44.73; H, 4.64; N, 5.99. Calcd for C I ~ H ~ I N ~ F ~ P F ~ :C, 44.96; H, 4.66;
N, 6.17.
l - F e ~ n y l m e t h y l - 2 - c h l o r o - 3 - e t h y l - 5 - ~ ~ y l i ~ d ~ l i u ~ ~ ~ u o r o
phosphate 7d (83%),m.p. 91-92 OC. 'H NMR (CDCb): 6 1.39 (t, J =7.4 Hz, 3H,
CHZCH~),3.00 (s, 3H, CH3). 4.20 (9.J = 7.4 Hz, 2H, CH2CH3). 4.25-4.27 (m, 7H,
Cp H), 4.38 (t, J = 1.5 Hz, 2H, Cp H), 5.10 (s,2H, Fc-CHz-), 6.99 (s, lH, 4-Im
H). I3C N M R ( c x b ) : 6 9.78 (NCHzCH3). 13.72 (CH3). 41.23 (NCH2CH3).
48.57 (Fc-CHz-),69.04-71.62 (Cp C-H and Cp C-C). 116.96 (C-Cl), 122.85 (5-Im
C), (2-Im C). Anal. Found: C, 42.05; H, 4.17; N, 5.86; C1, 7.13. Calcd for
C17HzoNzC~ePF6:C,41.79; H, 4.12; N, 5.73; c1.7.25.
l-Fe~nylmethyl-3butyllmidazoliumhexafluorophosphate 7e (88%). m.p.
123-124"C, 'H NMR (CDCb): 6 (t, J = 7.4 Hz, 3H, CH~CH~CHZCH~),(m, 2H,
CH~CHZCH~CH~),(m, 2H, CH~CHZCH~CH~),(m, 9H, Cp H and
CH2CH2CH2CH3),(t, J = 1.5 Hz, 2H. Cp H), (s,2H, Fc-CH~-),(s,2H, 4-ImH and
5-Im H), (s,lH, 2-Im H). I3CNMR (cDcl3): 6 12.82 (NCH2CH2CH2CH3), 18.61
(NCH2CH2CH2CH3), 30.85 (NCH2CH2CH2CH3). 46.72 (NCH~CH~CHZCH~),
49.23 (Fc-CHz-),68.70-71.57 (Cp C-H and Cp C-C), 121.36 (4-ImC), 121.58 (5-
Im C), 133.76 (2-Im C). Anal. Found: C, 45.91; H, 4.86; N, 5.73. Calcd for
C I S H ~ ~ N ~ F ~ P F ~ :C, 46.17; H, 4.95; N, 5.98.
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15. IMIDAZOLIUMSALTS 1877
1,3-di(Ferrucenylmethyl)imklamlium hexatluorophosphate 4 (80%). m.p.
150-152 OC, 'H NMR (cx13): 6 (s, 14H, Cp H), (s,4H. Cp H), (s,4H, FC-
CHz-), (s,2H, 4-Im H and 5-ImH), (s,lH, 2-Im H). 13CNMR (cDc13):6 49.85
(Fc-CH2-), 68.75-69.66 (Cp C-H and Cp C-C), 120.82 (Im C), 134.66 (2-Im C).
Anal. Found: C, 48.98; H, 4.14; N, 4.78; Fe, 18.09; F, 18.89. Calcd for
C~SH~SNZF~~PF~:C, 49.21; H. 4.13; N, 4.59; Fe. 18.31; F, 18.68.
REFERENCES
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
Hitchcock, P. B., Seddon, K. R. and Welton, T.,J. Chem SOC. Dalton
Tram., 1993,2639.
Hemnann,'W. A., Goossen, L. J., Kocher, C. and Artus, G. R. J., Angew.
Chem Int. Ed Engl., 1996,35.
Howarth,J., Hanlon, K., Fayne, D. and McCormac, P., Tetrahedron Lett.,
1997,17,3097.
Publicationin preparation.
Hauser,C. R. and Lindsay,J. K., J. Org. Chem,1956,21382.
Hauser,C. R. and Lindsay,J. K., J. Org. Chem,1957,22,355.
Bonhate, P., Dias, A., Papageorgiou, N., Kalyanasundaram, K. and
GrZ[tzel,M., Inorg. Chem, 1996,35, 1168.
Begtrup,M. and Larsen,P., Acta Chem Scund, 1990,40,1050.
Bublitz, D. E., J. Organometal. Chem. 1970,23,225.
Grimshaw. J. and Trocha-Grimshaw,J., J. Chem SOC., Perkin Trans. 2,
1991,751.
Downloadedby[NorthwesternUniversity]at15:2728December2014
16. 1878 HOWARTHETAL.
11. Arduengo JII,A. J., Harlow,R. L., and Kline, M.J. Am Chem Soc., 1991,
113,361.
Bildstein, B., Malaun, M.,Kopacka, H., Ongania, K-H. and Wurst, K., J.
Organometal.Chem,1998,552.45.
12.
Receivedin the UK 21 May 1999
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1,3-
Di(Ferrocenylmethyl)Imidazolium
and 1-Ferrocenylmethyl-3-
Alkylimidazolium Salts: A High
Yield and Facile Synthesis
J. Howarth
a
, J-L. Thomas
a
, K. Hanlon
a
& D.
McGuirk
a
a
School of Chemical Sciences, Dublin City
University , Dublin, 9, Ireland
Published online: 04 Dec 2007.
To cite this article: J. Howarth , J-L. Thomas , K. Hanlon & D. McGuirk (2000) 1,3-
Di(Ferrocenylmethyl)Imidazolium and 1-Ferrocenylmethyl-3-Alkylimidazolium Salts: A
High Yield and Facile Synthesis, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 30:10, 1865-1878, DOI:
10.1080/00397910008087232
To link to this article: http://dx.doi.org/10.1080/00397910008087232
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