Synthesis of tricarbonyl(diacetylarene)chromium and tricarbonyl(diformylarene)chromium complexes

Article abstract of DOI:10.1135/cccc20021616

Tricarbonylchromium complexes of diacetylbenzenes and 2,2′-diacetylbiphenyl were prepared in reasonable yields by direct complexation of the starting materials. Tricarbonyl-chromium complexes of diformylbenzenes and 2,2′-diformylbiphenyl were prepared in

Full text of DOI:10.1135/cccc20021616

1
616
Kmentová, Toma:
SYNTHESIS OF TRICARBONYL(DIACETYLARENE)CHROMIUM AND
TRICARBONYL(DIFORMYLARENE)CHROMIUM COMPLEXES
1
2,
Iveta KMENTOVÁ and Štefan TOMA *
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University,
SK-842 15 Bratislava, Slovak Republic; e-mail: 1 kmentova@fns.uniba.sk, toma@fns.uniba.sk
2
Received March 11, 2002
Accepted Septem ber 23, 2002
Tricarbon ylch rom ium com plexes of diacetylben zen es an d 2,2′-diacetylbiph en yl were pre-
pared in reason able yields by direct com plexation of th e startin g m aterials. Tricarbon yl-
ch rom ium com plexes of diform ylben zen es an d 2,2′-diform ylbiph en yl were prepared in good
yields by th e com plexation of th e correspon din g dioxolan es followed by acidic h ydrolysis of
th e protective groups.
Keyw ord s: Tricarbon ylch rom ium com plexes; Aren e com plexes; Aldeh ydes; Keton es;
Diacetylaren es; Diform ylaren es; Biaryls; Ch rom ium h exacarbon yl.
A n um ber of aren etricarbon ylch rom ium com plexes h as been described in
1
,2
th e literature , but m ost of th em are just m on osubstituted ben zen etri-
carbon ylch rom ium derivatives, wh ich were prepared by th e Pauson –
3
4
Mah affy or Top–Jaouen m eth od. Several years ago, we publish ed a m odi-
5
–8
fied m eth od for th e com plexation of aren es an d th eir derivatives , wh ich
works well for th e com plexation of som e arom atic keton es an d esters. Th e
m eth od con sists in h eatin g th e m ixtu re of an aren e, h exacarbon yl-
ch rom ium an d a catalyst (butyl acetate or eth yl form ate) in decalin to reflux
in a special adapter, wh ich precludes th e con tact of th e h ot reaction m ix-
ture with th e atm osph ere.
Th e m ain goal of th is work was to exam in e wh eth er th e m eth od is also
suitable for th e syn th esis of tricarbon ylch rom ium com plexes of diacetyl-
aren es an d diform ylaren es. From th is class of com poun ds, on ly an in effi-
cien t (10% yield) syn th esis of tricarbon yl(1,2-diacetylben zen e)ch rom ium
9
6
was described via m eth ylm agn esium iodide addition to tricarbon yl[η -
6
(
dim eth yl ph th alate)]ch rom ium . Sim ilarly, tricarbon yl(η -tereph th al-
aldeh yde)ch rom ium
9
,10
was prepared in a low yield via th e com plexation of
tereph th alaldeh yde tetraeth yl acetal an d subsequen t h ydrolysis. Th e syn -
6
th esis of tricarbon yl(η -ph th alaldeh yde)ch rom ium com plex was described
6
as a result of a com plex on e-pot reaction startin g from (η -ben zen e)tri-
Collect. Czech. Chem. Commun. (Vol. 67) (2002)
doi:10.1135/cccc20021616

Tricarbonylchromium Complexes
1617
carbon ylch rom ium 11. Th e tricarbon ylch rom ium com plex of 2,2′-(difor-
m yl)-6-m eth oxybiph en yl h as been prepared recen tly by th e Suzuki
6
couplin g of (η -2-brom o-6-m eth oxyben zaldeh yde)tricarbon ylch rom ium
with 2-form ylben zen eboron ic acid12
.
RESULTS AND DISCUSSION
We decided to exam in e th e direct com plexation of diacetylaren es with
Cr(CO) first. Th e com plexation s wen t sm ooth ly; th e results are depicted in
6
Sch em e 1. Th e yields of th e products stron gly depen ded on th e purity of
th e solven t (decah ydron aph th alen e), an d th e reagen ts (diacetylaren es an d
h exacarbon ylch rom ium ). For exam ple, we obtain ed 34–56% yields of crys-
6
tallin e tricarbon yl(η -1,3-diacetylben zen e)ch rom ium . It is in terestin g to
n ote th at th e m eth od could also be applied to a rapid syn th esis of
6
6
tricarbon yl(η -in dan -1-on e)ch rom ium (79% in 5 h ) an d tricarbon yl(η -
1
,2,3,4-tetrah ydron aph th alen -1-on e)ch rom ium (51% in 5 h ), wh ile tri-
6
carbon yl(η -1,2,3,4-tetrah ydron aph th alen -2-on e)ch rom ium was prepared
by th e com plexation of th e correspon din g dioxolan e . Direct com plex-
ation is n ot suitable for th e syn th esis of tricarbon yl(η -in dan e-1,3-dion e)-
1
3
6
ch rom ium , eith er; th is com poun d can on ly be prepared by th e com plex-
1
4,15
ation of th e bisdioxolan e derived from in dan e-1,3-dion e
.
R
R
COCH
3
Cr(CO)
6
COCH
3
∆
, (2–6 h)
Cr
decalin
CO
CO
1
, R = 2 - Ac
, R = 3 - Ac
, R = 4 - Ac
CO
2
3
4–56%
3
4, R = 2 -
Ac
SCHEME 1
Syn th esis of tricarbon yl(diacetylaren e)ch rom ium com plexes
It is well kn own th at th e direct com plexation of aren es h avin g an alde-
h yde fun ction al group is n ot possible an d th erefore we prepared th e
bisdioxolan es of th e correspon din g dialdeh ydes first. Th e protection of th e
aldeh yde groups wen t sm ooth ly an d gave h igh yields (72–84%) of th e
Collect. Czech. Chem. Commun. (Vol. 67) (2002)

1
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Kmentová, Toma:
bisdioxolan es. Th e com plexation of th e bisdioxolan es led to 52–88% iso-
lated yields of th e com plexes (Sch em e 2).
O
O
R
R
R
O
O
CHO
Cr(CO)6
H2SO4 / THF
∆,
2–6 h
Cr
Cr
decalin
CO
CO
CO
CO
CO
CO
O
72–84%
52–88%
5, R = 2 -
O
O
9, R = 2-CHO
6, R = 3 -
7, R = 4 -
8, R = 2 -
1
1
0, R = 3-CHO
O
O
1, R = 4-CHO
2, R = 2 -
1
O
OHC
O
O
SCHEME 2
Syn th esis of tricarbon yl(diform ylaren e)ch rom ium com plexes
Th e h ydrolysis of th e tricarbon ylch rom ium com plexes of th e bisdioxo-
lan es was often accom pan ied by th eir decom position . Th us, we ch ecked
1
6
several deprotection procedures usin g con cen trated HCl/aceton e , 85%
1
7
H PO /eth an ol , 85% H PO /n eutral alum in a an d m icrowave irradiation
3
4
3
4
1
8
19
(
MWI) , 4-m eth ylben zen e-1-sulfon ic acid (PTSA)/aceton e , but th e best
results were ach ieved usin g 50% H SO /THF
1
5
.
2
4
In sum m ary, we h ave succeeded in th e preparation of tricarbon yl-
ch rom ium com plexes of selected diacylaren es by direct com plexation , an d
developed a m eth od for th e syn th esis of th e com plexes of aren es possessin g
an aldeh yde m oiety.
EXPERIMENTAL
Ch em icals an d solven ts were purified by stan dard tech n iques. 1H an d 13C NMR spectra were
recorded for CDCl at room tem perature on a Varian Gem in i 2000 spectrom eter at 300 MHz
3
1
13
for H NMR an d 75 MHz for C NMR. Ch em ical sh ifts are given in δ relative to TMS (δ
ppm ) for 1H NMR an d CDCl3 (δ 77 ppm ) for C NMR. Couplin g con stan ts (J) are given in
Hz. IR spectra (waven um bers in cm ) were m easured on a Perkin –Elm er Paragon 1000 FT-IR
spectrom eter. All m eltin g poin ts are un corrected, an d were m easured on a Koffler h ot-plate
apparatus. All com plexation s were carried out in a reactor described previously
13
0
–
1
5
–8
.
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Tricarbonylchromium Complexes
1619
Gen eral Procedure for th e Com plexation of Diacetylaren es (1–4)
A solution of th e correspon din g diacetylaren e (3 m m ol) an d Cr(CO)6 (0.66 g, 3 m m ol) in
decah ydron aph th alen e (≈70 m l) un der Ar was h eated at reflux at bath tem perature of 265 °C
(
Wood m etal bath ) with a catalytic am oun t of eth yl form ate (1 m l). Followin g th e evolution
3
of a calculated am oun t of CO (≈200 cm ), th e reaction m ixture was cooled to room tem pera-
ture, filtered th rough a pad of silica gel, wash ed with h exan e (rem ovin g decah ydro-
n aph th alen e) an d th e product was eluted with Et O. Th e solven t was evaporated an d th e
2
residue purified by flash -ch rom atograph y (SiO , h exan e–eth yl acetate 3:1) an d recrystallized
2
from h exan e–Et O m ixture.
2
6
Tricarbonyl(η -1,2-diacetylbenzene)chromium (1): 232 m g (26%) of oran ge crystals was iso-
9
1
lated, m .p. 63 °C (in accord with ref. ). IR: 1972, 1896, 1678, 1252. H NMR: 2.48 s, 6 H
(
1
3
COCH ); 5.42–5.47 m , 2 H (Hβ); 5.50–5.55 m , 2 H (Hα). C NMR: 28.6, 90.8, 91.0, 105.0,
3
1
3
97.7, 229.7. For C13H10CrO5 (298.2) calculated: 52.36% C, 3.38% H; foun d: 52.30% C,
.32% H.
6
Tricarbonyl(η -1,3-diacetylbenzene)chromium (2): 304 m g (34%) of oran ge crystals was iso-
1
lated, m .p. 118–120 °C. IR: 1975, 1903, 1681, 1220. H NMR: 2.51 s, 6 H (COCH ); 5.32 t, 1 H,
3
3
3
4
4
13
J4,5
= J5,6 = 6.6 (H5); 6.32 dd, 2 H (H4,6); 6.72 d, 1 H, J2,4 = J2,6 = 1.3 (H2). C NMR:
2
3
5.7, 87.6, 94.4, 94.4, 95.4, 194.2, 228.0. For C13H10CrO5 (298.2) calculated: 52.36% C,
.38% H; foun d: 52.27% C, 3.25% H.
6
Tricarbonyl(η -1,4-diacetylbenzene)chromium (3): 179 m g (20%) of red crystals was obtain ed,
1
m .p. 125–127 °C. IR: 1974, 1901, 1683, 1260. H NMR: 2.51 s, 6 H (COCH ); 6.00 s, 4 H
3
1
3
(
H-Ar). C NMR: 25.8, 91.4, 97.9, 195.5, 229.4. For C13H10CrO5 (298.2) calculated: 52.36% C,
3
.38% H; foun d: 52.28% C, 3.22% H.
Tricarbonyl(η -2,2′-diacetylbiphenyl)chromium (4): 258 m g (23%) of oran ge crystals was iso-
6
1
lated, m .p. 113–115 °C. IR: 1963, 1883, 1685, 1246. H NMR: 2.18 s, 3 H (COCH *); 2.49 s,
3
1
3
3
4
H (COCH ); 5.27 dd, 1 H, J5,6 = 6.0, J4,6 = 1.4 (H6*); 5.50–5.60 m , 2 H (H4,5*); 5.75 dd,
3
3
4
H, J3,4 = 6.1, J3,5 = 1.4 (H3*); 7.49–7.79 m , 4 H (H-Ar) (* correspon din g to th e ch em ical
1
3
sh ifts of th e com plexed ben zen e m oiety). C NMR: 28.2, 28.7, 91.1, 91.2, 92.5, 96.5, 102.2,
16.2, 127.8, 128.9, 130.9, 131.2, 138.8, 140.8, 197.4, 200.0, 231.5. For C19H14CrO5 (374.3)
1
calculated: 60.97% C, 3.77% H; foun d: 60.91% C, 3.80% H.
Gen eral Procedure for th e Preparation of Dioxolan es from th e Corespon din g Aldeh ydes
A solution of a dialdeh yde (10 m m ol), eth ylen e glycol (1.3 m l, 22 m m ol, 1.1 equivalen t)
an d a catalytic am oun t of 4-m eth ylben zen e-1-sulfon ic acid (5 m g) in ben zen e (20 m l) was
h eated at reflux un der a con den ser equipped with th e Dean –Stark trap for 15 h . Th e reac-
tion m ixture was cooled to room tem perature, wash ed with 5% NaOH solution an d th e wa-
ter layer extracted with ben zen e (20 m l). Th e com bin ed organ ic layers were dried over
an h ydrous K CO , an d th e solven t evaporated. Th e residue was purified as described below.
2
3
1
,2-Di(1,3-dioxolan-2-yl)benzene: bulb-to-bulb distillation afforded 1.86 g (84%) of a color-
1
less liquid, b.p. 160 °C/130 Pa. IR: 667, 731, 1073, 1191, 1285, 1373, 1445, 2885. H NMR:
.02–4.17 m , 8 H (OCH CH O); 6.24 s, 2 H (CH); 7.39 m , 2 H (Hβ); 7.64 m , 2 H
4
(
6
2
2
1
3
Hα). C NMR: 63.45, 102.92, 129.20, 127.69, 138.30. For C12H14O4 (222.2) calculated:
4.85% C, 6.35% H; foun d: 64.82% C, 6.33% H.
,3-Di(1,3-dioxolan-2-yl)benzene: bulb-to-bulb distillation afforded 1.82 g (82%) of a color-
1
1
less liquid, b.p. 180°C/130 Pa. IR: 678, 732, 1074, 1194, 1244, 1372, 1447, 2881. H NMR:
.99–4.13 m , 8 H (OCH CH O); 5.83 s, 2 H (CH); 7.37 m , 1 H (H5); 7.46–7.49 m , 2 H
3
2
2
Collect. Czech. Chem. Commun. (Vol. 67) (2002)

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Kmentová, Toma:
(
H4,6); 7.59 bs, 1 H (H2). 13C NMR: 65.11, 103.31, 124.44, 127.07, 128.25, 138.39. For
C12H14O4 (222.2) calculated: 64.85% C, 6.35% H; foun d: 64.90% C, 6.37% H.
,4-Di(1,3-dioxolan-2-yl)benzene: recrystallization from a h exan e–eth yl acetate m ixture
1
2
0
gave 1.80 g (81%) of a pale yellow crystallin e com poun d, m .p. 89–90 °C (ref. gives m .p.
9–90 °C). 1H NMR: 4.02–4.11 m , 8 H (OCH CH O); 5.84 s, 2 H (CH); 7.50 s, 4 H (H-Ar).
8
2
2
2
,2′-Di(1,3-dioxolan-2-yl)bifenyl: flash ch rom atograph y (SiO , h exan e–eth yl acetate 5:1)
2
an d subsequen t recrystallization from h exan e furn ish ed 2.15 g (72%) of a colorless crystal-
2
1
1
lin e com poun d, m .p. 52 °C (ref.
gives m .p. 52 °C).
H NMR: 3.80–4.06 m , 8 H
(
OCH CH O); 5.50 s, 2 H (CH); 7.24 m , 2 H (H6); 7.38–7.43 m , 4 H (H4,5); 7.67 m , 2 H (H3).
2
2
Gen eral Procedure for th e Com plexation of Di(1,3-dioxolan -2-yl)aren es 5–8
A solution of th e correspon din g bisdioxolan e (3 m m ol) an d Cr(CO)6 (0.66 g, 3 m m ol) in
decah ydron aph th alen e (≈70 m l) un der Ar was h eated at bath tem perature of 265 °C with
a catalytic am oun t of eth yl form ate (1 m l). Followin g th e evolution of a calculated am oun t
3
of CO (≈200 cm ), th e reaction m ixture was cooled to room tem perature, filtered th rough
a pad of silica gel, wash ed with h exan e (rem ovin g decah ydron aph th alen e) an d th e product
was eluted with Et O. Th e solven t was evaporated an d th e residue purified as described below.
2
6
Tricarbonyl[η -1,2-di(1,3-dioxolan-2-yl)benzene]chromium (5): recrystallization from h exan e–
eth yl acetate gave 0.76 g (71%) of a yellow crystallin e product, m .p. 96–98 °C. IR: 1960,
1
5
875, 1108, 1063. 1H NMR: 4.05–4.17 m , 8 H (OCH CH O); 5.33–5.36 m , 2 H (Hβ);
.65–5.68 m , 2 H (Hα); 5.99 s, 2 H (CH). C NMR: 66.0, 66.1, 89.8, 91.4, 99.6, 106.3, 232.0.
2 2
1
3
For C15H14CrO7 (358.3) calculated: 50.29% C, 3.94% H; foun d: 50.39% C, 3.94% H.
6
Tricarbonyl[η -1,3-di(1,3-dioxolan-2-yl)benzene]chromium (6): flash ch rom atograph y (SiO ,
2
h exan e–eth yl acetate 4:1) an d recrystallization from h exan e–eth yl acetate afforded 0.77 g
(
72%) of a yellow crystallin e product, m .p. 109–110 °C. IR: 1962, 1877, 1167, 1100.
1
3
3
H NMR: 4.00–4.18 m , 8 H (OCH CH O); 5.26 t, 1 H, J4,5
=
J5,6 = 6.5 (H5); 5.55 d, 2 H
H4,6); 5.59 s, 2 H (CH); 5.76 s, 1 H (H2). C NMR: 66.0, 89.4, 90.1, 91.8, 101.6, 106.0,
31.7. For C15 14CrO7 (358.3) calculated: 50.29% C, 3.94% H; foun d: 50.21% C, 3.97% H.
2
2
1
3
(
2
H
6
Tricarbonyl[η -1,4-di(1,3-dioxolan-2-yl)benzene]chromium (7): recrystallization from h exan e–
eth yl acetate afforded 0.77 g (72%) of an oran ge yellow solid, m .p. 151–153 °C. IR: 1961,
1
2
5
1
902, 1882, 1106, 1076. H NMR: 4.02–4.13 m , 8 H (OCH CH O); 5.50 s, 4 H (H-Ar); 5.58 s,
2 2
1
3
H (CH). C NMR: 66.0, 89.8, 101.5, 107.8, 231.8. For C15H14CrO7 (358.3) calculated:
0.29% C, 3.94% H; foun d: 50.21% C, 3.92% H.
6
Tricarbonyl[η -2,2′-di(1,3-dioxolan-2-yl)biphenyl]chromium (8): recrystallization from h exan e–
eth yl acetate furn ish ed 0.81 g (62%) of a yellow crystallin e product, m .p. 163–164 °C. IR:
1
3
3
1
6
5
6
2
960, 1873, 1107, 1071. H NMR: 3.83–4.13 m , 8 H (OCH CH O); 5.20 dt, 1 H, J3,4
=
J4,5
=
2
2
.4, J4,6 = 1.0 (H4*); 5.31 s, 1 H (CH*); 5.48 dd, 1 H, 3J5,6 = 6.4 (H6*); 5.57 d, 1 H (H3*);
.63 dd, 1 H (H5*); 5.72 s, 1 H (CH); 7.38–7.56 m , 4 H (H-Ar). C NMR: 65.3, 65.8, 66.0,
6.2, 85.8, 87.7, 94.9, 98.9, 100.3, 101.6, 110.0, 111.9, 126.1, 129.2, 133.6, 133.9, 137.8,
32.3. For C21H18CrO7 (434.4) calculated: 58.07% C, 4.18% H; foun d: 58.09% C, 4.15% H.
4
1
3
6
Gen eral Procedure for th e Preparation of Tricarbon yl(η -aren edicarbaldeh yde)ch rom ium (0)
Com plexes by Hydrolysis (9–12)
A solution of a dioxolan e com plex (0.28 m m ol) in THF (4 m l) was purged with Ar un der
stirrin g, an d a 50% aqueous H SO (2 m l) was added dropwise via a syrin ge at room tem per-
2
4
ature. Th e reaction m ixture was stirred for 3 h , water (4 m l) was added, an d th e resultan t
Collect. Czech. Chem. Commun. (Vol. 67) (2002)

Tricarbonylchromium Complexes
1621
m ixture was extracted with Et O (3 × 10 m l). Th e organ ic layer was wash ed with a saturated
2
Na CO solution (10 m l), dried over an h ydrous Na SO an d th e solven t evaporated. Th e res-
2
3
2
4
idue was purified as described below.
6
Tricarbonyl(η -phthalaldehyde)chromium (9): flash ch rom atograph y (SiO , h exan e–eth yl ace-
2
9
tate 4:1) gave 67 m g (88%) of dark-red crystals, m .p. 68 °C (ref. gives m .p. 69 °C). IR: 1976,
1
(
899, 1681, 1172. 1H NMR: 5.65–5.70 m , 2 H (Hβ); 5.87–5.92 m , 2 H (Hα); 10.20 s, 1 H
CHO). 13C NMR: 92.1, 92.4, 96.9, 189.7, 228.6. For C H CrO (270.2) calculated: 48.90% C,
11 6 5
2
.24% H; foun d: 48.79% C, 2.12% H.
Tricarbonyl(η -isophthalaldehyde)chromium (10): recrystallization from h exan e–dieth yl eth er
6
1
afforded 56 m g (75%) of red crystals, m .p. 97–98 °C. IR: 1984, 1917, 1688, 1123. H NMR:
5
9
.39 t, 1 H, 3J4,5
=
3
J
= 6.4 (H5); 6.25 dd, 2 H (H4,6); 6.51 d, 1 H, J2,4 = J2,6 = 1.2 (H2);
4
4
5,6
1
3
.55 s, 2 H (CHO). C NMR: 87.7, 93.6, 95.1, 95.4, 187.0, 227.0. For C11H CrO (270.2) cal-
6
5
culated: 48.90% C, 2.24% H; foun d: 48.81% C, 2.22% H.
6
Tricarbonyl(η -terephthalaldehyde)chromium (11): flash ch rom atograph y (SiO , h exan e–eth yl
2
acetate 2:1) an d recrystallization from h exan e–dieth yl eth er furn ish ed 60 m g (80%) of red
1
0
crystals, m .p. 105–107 °C (ref.
gives m .p. 107–108 °C). IR: 1982, 1910, 1694, 1207.
1
H NMR: 9.94 s, 4 H (H-Ar); 9.65 s, 1 H (CHO). 13C NMR: 91.6, 96.8, 188.6, 228.3. For
C11H CrO (270.2) calculated: 48.90% C, 2.24% H; foun d: 48.84% C, 2.13% H.
6
5
6
Tricarbonyl(η -biphenyl-2,2′-dicarbaldehyde)chromium (12): flash ch rom atograph y (SiO ,
2
h exan e–eth yl acetate 5:2) an d recrystallization from h exan e–dieth yl eth er gave 51 m g (52%)
1
3
4
of a red solid, m .p. 93–95 °C. IR: 1968, 1891, 1691. H NMR: 5.36 dd, 1 H, J5,6 = 6.1, J4,6
=
.6 (H6*); 5.60–5.69 m , 2 H (H4,5*); 5.96 dd, 1 H, 3J = 6.0, J3,5 = 1.7 (H3*); 7.68–7.94 m ,
H (H-Ar); 9.42 s, 1 H (CHO*); 10.00 s, 1 H (CHO). C NMR: 89.5, 91.7, 92.2, 95.5, 96.7,
14.4, 130.1, 132.9, 134.1, 134.4, 134.6, 135.6, 188.3, 191.1, 230.5. For C17H10CrO5 (346.3)
4
1
4
1
3,4
1
3
calculated: 58.97% C, 2.91% H; foun d: 58.92% C, 2.85% H.
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1
2
. Wilkinson G., Stone F. G. A., Abel E. W. (Eds): Comprehensive Organometallic Chemistry I,
Vol. 3. Pergamon Press, Oxford 1982.
. Abel E. W., Stone F. G. A., Willkinson G. (Eds): Comprehensive Organometallic Chemistry II,
Vol. 5. Pergamon Press, Oxford 1995.
3
4
5
6
7
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