Syntheses and structures of 9-bromo-10-diphenylphosphanylanthracene and its oxidation products

Article abstract of DOI:10.1515/znb-2007-0514

Treatment of 9,10-dibromoanthracene with one mole equivalent of n-butyllithium and chlorodiphenylphosphane yields 9-bromo-10- diphenylphosphanylanthracene (1). Oxidation of 1 with chalcogens leads to {Br(C₁₄H₈)(Ph₂P=E)} wi

Full text of DOI:10.1515/znb-2007-0514

Syntheses and Structures of 9-Bromo-10-diphenylphosphanylanthracene
and its Oxidation Products
Gerald Schwab, Daniel Stern, Dirk Leusser, and Dietmar Stalke
Institut fu¨r Anorganische Chemie der Universita¨t Go¨ttingen, Tammannstraße 4, 37077 Go¨ttingen,
Germany
Reprint requests to Prof. Dr. Dietmar Stalke. E-mail: dstalke@chemie.uni-goettingen.de
Z. Naturforsch. 2007, 62b, 711 – 716; received October 27, 2006
Treatment of 9,10-dibromoanthracene with one mole equivalent of n-butyllithium and chlorodi-
phenylphosphane yields 9-bromo-10-diphenylphosphanylanthracene (1). Oxidation of 1 with chalco-
gens leads to {Br(C14H8)(Ph2P=E)} with E = O (2), S (3) and Se (4). The syntheses and structure
determinations of the parent compound 1 and the oxidized species 2 – 4 are reported.
Key words: Anthracene, Asymmetrical Synthesis, Phosphane, Phosphorylation, Selenium
Introduction
9,10-Dibromoanthracene (A in Scheme 1) is a
common reactant to obtain anthracene derivatives,
both symmetrically and asymmetrically substituted
in the 9- and 10-positions. However, reports on 10-
heterosubstituted 9-bromoanthracenes of type B are
rare. In almost all cases published so far, the com-
pounds are bearing nitrogen, oxygen, boron or sili-
con in position 10; phosphorus derivatives of type C
are completely unknown, although such compounds
would be of great synthetic interest as the remaining
halogen atom should be easily replaceable by various
substituents.
Yamaguchi et al. synthesized a 9-bromo-10-boryl-
anthracene as an intermediate for trianthrylboranes [1],
and more recently they reported on a B,Bꢀ,Bꢀꢀ-tris(10-
bromoanthryl)borazine derivative which can be used
as a key precursor for a variety of 10-substituted 9-
anthrylborazins [2]. The palladium-catalyzed reaction
of A with secondary amines can be performed without
the use of strong bases to obtain the corresponding 9-
bromo-10-aminoanthracene selectively [3, 4]. Another
example of a group 15 substituted bromoanthracene
is a bromoanthrylcarbazole whose structure was deter-
mined in the early 1990s [5].
Scheme 1. Heterosubstituted anthracenes. R = BRꢀ2, NRꢀ2,
ORꢀ, SiRꢀ3; Rꢀ = alkyl, aryl.
like self-assembly and molecular recognition [6, 7],
the method is restricted to the formation of symmet-
rically substituted anthracene derivatives and so far
no attempts were made to replace only one bromo-
substituent of A by a PR2 group to give C.
The first 9-phosphanyl substituted anthracene was
synthesized by Akasaka et al. in the reaction of lithium
diphenylphosphanide and 9-bromoanthracene [8]. Its
ligand properties in transition metal chemistry were in-
vestigated and the [4+4] dimerization upon irradiation
was observed [9]. 1,8-Bis(diphenylphosphanyl)anthr-
acene serves as a chelating neutral donor ligand in tran-
sition metal chemistry [10], and recently the synthe-
sis of the symmetrically substituted 9,10-bis(diphenyl-
phosphanyl)anthracenewas communicated. Upon gold
complexation a flexible cyclic [Au{C14H8(Ph2P)2}]3
trication is formed [6].
Treating 9,10-dibromoanthracene with two equiva-
lents of BuLi leads to 9,10-dilithioanthracene which
Results and Discussion
n
We reported the synthesis and oxidation of the par-
ent 9,10-bis(diphenylphosphanyl)anthracene, to give
the products {C14H8(Ph2P)2}, {C14H8(Ph2P=O)2},
{C14H8(Ph2P=S)2}, and {C14H8(Ph2P=Se)2} [11].
can react with a variety of electrophiles to give sym-
metrically substituted compounds. Although the re-
action was also used to form P–C-bonds, and the
disubstituted compounds feature interesting properties
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G. Schwab et al. · 9-Bromo-10-diphenylphosphanylanthracene and its Oxidation Products
Fig. 1. Molecular structures
of 1 – 4. For 3 and 4 only
one of the two crystallographi-
cally independent molecules is
shown. Anisotropic displace-
ment parameters are drawn at
the 50 % probability level. Hy-
drogen atoms are omitted for
clarity.
Br
Br
Br
Br
nBuLi
PClPh2
2: E = O, Ox = H2O2·urea
3: E = S, Ox = sulfur
[Ox]
- nBuBr
- LiCl
4: E = Se, Ox = selenium
PPh2
PPh2
Scheme 2. Syntheses of com-
pounds 1 – 4.
E
1
Surprisingly, the sulfur oxidized species is a solid-state stituted compound, the solubility of 1 in diethyl ether
fluorescent chemosensor for toluene. The host/guest is very good and insoluble by-products can easily be
complex of {C14H8(Ph2P=S)2} and toluene (mole ra- removed by filtration.
tio 1 : 2) shows a very intense green fluorescence
in the solid state at 508 nm (λex = 380 nm). In
the course of designing novel chemosensors [12]
we have now isolated and characterized {Br(C14H8)
(Ph2P)} (1) as the first 9-bromo-10-phosphanylanthra-
cene. In addition, we describe here the preparation
and structure determination of the oxidized derivatives
{Br(C14H8)(Ph2P=O)} (2), {Br(C14H8)(Ph2P=S)} (3),
and {Br(C14H8)(Ph2P=Se)} (4).
The oxidation reactions of 1 were performed ac-
cording to literature methods [14]. For the syn-
thesis of 2 (E = O) the mild oxidizing agent
H2O2·(H2N)2C=O was used at r. t. in dichloromethane.
The reaction of 1 with elemental sulfur and gray sele-
nium in toluene at reflux gave 3 (E = S) and 4 (E = Se),
respectively. All oxidation products were obtained in
high yields. The δ(31P) chemical shifts of the phospho-
rus atoms in 1 – 4 are similar to the values published for
Lithiation of 9,10-dibromoanthracene with one the 9,10-diphosphanyl-substituted analogues [11]. All
n
equivalent of BuLi leads to a mono-lithiated bromo- compounds were isolated as crystalline yellow solids
anthracene [13] which was reacted in situ with a and their identities were established by elemental anal-
stoichiometric amount of chlorodiphenylphosphane yses, mass spectrometry, NMR spectroscopy (31P, 1H,
(Scheme 2). In contrast to the 9,10-diphosphanyl-sub- 77Se) and single crystal X-ray diffraction.
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G. Schwab et al. · 9-Bromo-10-diphenylphosphanylanthracene and its Oxidation Products
713
Fig. 2. Superposition plots of 2
(solid lines) and 3 (dashed
lines) fitted by employing
the C4a, C8a, C9a and C10a
positions viewed from the
side (a) and along the P1–C10
bond (b).
Table 1. Selected bond lengths (pm) and angles (deg) of 1 – 4.
2 (E = O) 3 (E = S) 4 (E = Se)
C1–C2 and one P–Cipso−Ph bond is close to zero for
the unsubstituted vicinal position 2 [15], a larger sub-
stituent causes the same bisectional orientation [16]
like in 1 and 2.
1
Br1–C9
P1–C10
P1–E1
190.40(17) 189.9(2)
184.50(17) 183.8(2)
190.2(3)
182.6(3)
190.2(4)
183.3(3)
148.93(18) 195.48(10) 211.23(11)
Differently, the two phenyl substituents of 3 and 4
are oriented towards the same side of the anthracene
chromophore. The P=E bonds are arranged almost or-
thogonally relative to the anthracene plane with torsion
angles of 86.7◦ in 3 and 87.5◦ in 4. A superposition
of 2 and 3 depicted in different projections is shown
in Fig. 2. The different orientations of the Ph2P=O and
the Ph2P=S substituents are obvious.
The anthracene moiety in 1 is slightly folded (an-
gle along C9···C10 = 177.4◦), while the boat-like con-
formation is more distinct in 2 – 4 due to the different
orientations of the Ph2P=E substitutents (folding an-
gle 163.0◦ in 4). The cisoid orientations of the phenyl
substituents in 3 and 4 cause the two lateral anthracene
rings to bend towards the sulfur and selenium atom, re-
spectively. The bromine and phosphorus atoms are not
located in the best plane of the central anthracene C6
perimeter and the deviation from the plane increases
drastically when proceeding from 2 (transoid) to 3
and 4 (cisoid).
P1–C15
P1–C21
183.20(18) 181.1(3)
182.73(18) 181.0(3)
182.7(3)
183.2(3)
183.3(4)
182.4(4)
out-of-planea Br/P 1.16/4.98 2.23/6.41 7.00/10.45 6.93/10.23
folding angle Anb 177.4
170.8
162.7
163.0
a
Angle of the Br–C and P–C10 bond to the C9···C10 vector of the
anthracene moiety; b angle included by the two outer C6-perimeters.
The results of the structure determinations of 1 – 4
are shown in Fig. 1, selected bond lengths and angles
are given in Table 1. The crystal data and the experi-
mental parameters used for the crystal structure analy-
ses are listed in Table 2.
All compounds crystallize in the monoclinic space
group P21/n. The asymmetric units of 1 and 2 contain
one molecule, while those of the derivatives 3 and 4
show two molecules. Different to the oxidized 9,10-
disubstituted analogues, 1 – 4 crystallize without any
interstitial solvent molecules in the crystal. The bond
lengths and angles and the conformations of the Ph2P
and Ph2P=E substituents of 1 – 4 are very similar to
those in the disubstituted derivatives.
The molecules of 1 and 2 have the same orientation
of the Ph2P and Ph2P=O substituents relative to the
anthracene plane, each with one phenyl group on either
Conclusions
In conclusion, the 9-bromo-10-phosphanylanthra-
side. The anthracene plane bisects the Ph–P–Ph bond cenes {Br(C14H8)(Ph2P)} (1), {Br(C14H8)(Ph2P=O)}
angle in 1 (106.3◦), and the oxygen atom in 2 is almost (2), {Br(C14H8)(Ph2P=S)} (3), and {Br(C14H8)(Ph2
in plane (O–P–C10–C4a torsion angle 18.1◦). This P=Se)} (4) can easily be synthesized in high yields
alignment of the phenyl substituents corresponds to using common reagents. Their spectral and structural
the structures of analogous 1-phosphanylnaphthalenes. properties are widely in accord with the 9,10-diphos-
While the dihedral angle between the naphthalene phanyl compounds, but they do not crystallize as host
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714
G. Schwab et al. · 9-Bromo-10-diphenylphosphanylanthracene and its Oxidation Products
molecules for toluene like their diphosphanyl ana- and dried with magnesium sulfate over night. After filtra-
tion and removal of the solvent, the product is obtained
as yellow crystals by recrystallization from toluene. Yield:
logues do. The monofunctional derivatives open the
door for the syntheses of asymmetrically substituted
anthracenes with mixed P/B, P/C, P/Si or P/N cen-
tered substituents. Our future work is aimed to evaluate
how these changes will influence the sensoric and pho-
tonic properties of the related host/guest complexes.
Metal complexes of d and f block elements will also
be investigated.
◦
310 mg (91 %). – M. p. 164 C. – 1H NMR (500.13 MHz,
3
CDCl3): δ = 8.64 (d, JHH = 8.93 Hz, 2H, H1,8, An),
3
8.59 (d, JHH = 8.92 Hz, 2H, H4,5, An), 7.68 – 7.63 (m,
4H, Hortho, Ph), 7.52 – 7.46 (m, 4H, H2,7, An / Hpara
,
3
Ph), 7.40 – 7.36 (m, 4H, Hmeta, Ph), 7.23 (ddd, JHH
=
3
4
8.92 Hz, JHH = 6.66 Hz, JHH = 1.20 Hz, 2H, H3,6, An).
1
–
31P{ H} NMR (202.46 MHz, CDCl3): δ = 31.6 (s). – MS
(EI, 70 eV): m/z (%) = 457 (100) [M]+, 377 (26) [M–Br]+,
201 (8) [P(O)Ph2]+, 185 (21) [PPh2]+, 176 (17) [C14H8]+.
– C26H18BrOP (457.30): calcd. C 68.29, H 3.97; found
C 68.04, H 4.05.
Experimental Section
The syntheses were performed under an inert gas atmo-
sphere of dry nitrogen with Schlenk techniques. All sol-
vents were dried and purified according to standard proce-
dures and stored under nitrogen. 1D and 2D NMR spectra
were obtained on a Bruker Avance 500 instrument operat-
9-Bromo-10-(diphenylthiophosphoryl)anthracene (3)
Elemental sulfur (80 mg, 2.50 mmol) is added to a so-
lution of 1 (1.10 g, 2.49 mmol) in 30 mL of toluene. The
reaction mixture is then heated to reflux for 4 h. After re-
moval of the solvent the product is obtained by crystalliza-
tion of the residue from diethyl ether. Yield: 1.10 g (93 %). –
M. p. 181 ◦C. – 1H NMR (500.13 MHz, CDCl3): δ = 8.55 (d,
3JHH = 8.90 Hz, 2H, H1,8, An), 8.04 (d, 3JHH = 8.84 Hz, 2H,
1
ing at 500.13, 202.46, and 95.38 MHz, respectively, for H,
31P, and 77Se. Melting points were measured in sealed capil-
laries using a Bu¨chi melting point instrument. Mass spectra
were recorded on a MAT 95 spectrometer. Elemental anal-
yses were performed by Analytisches Labor, Anorganische
Chemie, Go¨ttingen.
H4,5, An), 7.72 – 7.67 (m, 4H, Hortho, Ph), 7.40 (ddd, 3JHH
8.90 Hz, JHH = 6.54 Hz, JHH = 0.70 Hz, 2H, H2,7, An),
=
9-Bromo-10-(diphenylphosphanyl)anthracene (1)
3
4
7.29 – 7.26 (m, 2H, Hpara, Ph), 7.23 – 7.20 (m, 4H, Hmeta
,
nBuLi in n-hexane (1.37 mL, 2.22 M, 3.04 mmol) is
added to a suspension of 9,10-dibromoanthracene (1.00 g,
2.98 mmol) in 25 mL of diethyl ether at −15 ◦C. The reaction
mixture is stirred for 30 min before addition of chlorodiphen-
ylphosphane (660 mg, 2.99 mmol). The suspension is stirred
for 30 min and insoluble products are removed by filtration.
After removal of the solvent, the product is obtained as a yel-
low powder. Crystals are obtained from a saturated solution
in diethyl ether upon◦a few days’ storage at r. t. Yield: 1.17 g
3
3
4
Ph), 7.01 (ddd, JHH = 8.84 Hz, JHH = 6.54 Hz, JHH
=
1
1.03 Hz, 2H, H3,6, An). – 31P{ H} NMR (202.46 MHz,
CDCl3): δ = 34.7 (s). – MS (EI, 70 eV): m/z (%) = 474 (100)
[M]+, 363 (25) [M–SPh]+, 286 (17) [Br(C14H8)P]+, 185
(86) [PPh2]+, 176 (12) [C14H8]+. – C26H18BrPS (473.36):
calcd. C 65.97, H 3.83; found C 64.54, H 4.08.
9-Bromo-10-(diphenylselenophosphoryl)anthracene (4)
1
(89 %). – M. p. 156 C. – H NMR (500.13 MHz, CDCl3):
δ = 8.84 (dd, 3JHH = 9.00 Hz, 4JHP = 5.33 Hz, 2H, H4,35, An),
This compound was prepared in analogy to 3 from 1
(240 mg, 0.54 mmol) and an excess of gray selenium
(120 mg, 1.52 mmol) in 30 mL of toluene and subsequent
crystallization of the product from toluene. Yield: 230 mg
3
8.66 (d, JHH = 8.85 Hz, 2H, H1,8, An), 7.54 (ddd, JHH
=
3
4
8.88 Hz, JHH = 6.50 Hz, JHH = 1.09 Hz, 2H, H2,7, An),
3
7.41 – 7.37 (m, 4H, Hortho, Ph), 7.33 (ddd, JHH = 9.00 Hz,
◦
1
3JHH = 6.50 Hz, 4JHH = 1.20 Hz, 2H, H3,6, An), 7.27 – 7.22
(81 %). – M. p. 235 C. – H NMR (500.13 MHz, CDCl3):
δ = 8.59 (d, 3JHH = 8.92 Hz, 2H, H1,8, An), 8.08 (d, 3JHH
8.92 Hz, 2H, H4,5, An), 7.79 – 7.74 (m, 4H, Hortho, Ph), 7.44
(m, 6H, Hmeta/para, Ph). – 31P{ H} NMR (202.46 MHz,
1
=
CDCl3): δ = −22.7 (s). – MS (EI, 70 eV): m/z (%) =
442 (100) [M]+, 361 (35) [M–Br]+, 207 (10) [C14H8P]+,
176 (24) [C14H8]+. – C26H18BrP (441.30): calcd. C 70.76,
H 4.11; found C 70.71, H 4.73.
3
3
4
(ddd, JHH = 8.92 Hz, JHH = 6.70 Hz, JHH = 0.72 Hz,
2H, H2,7, An), 7.33 – 7.29 (m, 2H, Hpara, Ph), 7.26 – 7.22
3
3
(m, 4H, Hmeta, Ph), 7.07 (ddd, JHH = 8.92 Hz, JHH
=
6.70 Hz, JHH = 1.06 Hz, 2H, H3,6, An). – 31P{ H} NMR
4
1
(202.46 MHz, CDCl3): δ = 25.9 (s). – 77Se{ H} NMR
1
9-Bromo-10-(diphenylphosphoryl)anthracene (2)
1
(95.38 MHz, CDCl3): δ = −281.1 (d, JSeP = 734.9 Hz).
An excess of H2O2·(H2N)2C=O (300 mg, 3.19 mmol) is – MS (EI, 70 eV): m/z (%) = 520 (59) [M]+, 442 (100)
added to a solution of 1 (330 mg, 0.75 mmol) in 40 mL of [M–Se]+, 363 (62) [M–SePh]+, 185 (57) [PPh2]+, 176 (32)
dichloromethane. The reaction mixture is stirred for 1 h and [C14H8]+. – C26H18BrPSe (520.26): calcd. C 60.02, H 3.49;
then filtered. The filtrate is washed with water (2 × 10 mL) found C 60.19, H 3.64.
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G. Schwab et al. · 9-Bromo-10-diphenylphosphanylanthracene and its Oxidation Products
715
Table 2. Crystal Data and
Structure Refinement for
1 – 4.
Compound
CCDC number
Empirical formula
Formula mass
T [K]
Space group
a [pm]
b [pm]
1
2
3
4
610420
26H18BrP
610421
C26H18BrOP
457.30
610422
C26H18BrPS
473.36
610423
C26H18BrPSe
520.26
133(2)
C
441.30
100(2)
P21/n
928.19(6)
1687.62(11)
1258.22(8)
91.2870(10)
1.9704(2)
4
a
100(2)
P21/n
100(2)
P21/n
R1
wR2
=
Σ||Fo| − |Fcꢁ/Σ|Fo|;
[Σw(Fo − Fc2)2/
b
2
P21/n
=
Σw(Fo2)2]1/2
;
w = [σ2(Fo
)
c
2
944.01(5)
1682.77(9)
1265.86(7)
92.7740(10)
2.00853(19)
4
1723.27(11)
1392.49(9)
1733.47(11)
90.4330(10)
4.1596(5)
8
1717.1(3)
1414.5(3)
1737.8(4)
90.90(3)
4.2203(15)
8
+ (g1P)2 + g2P]−1, P = 1/3
[max(Fo2,0) + 2Fc2].
c [pm]
β [deg]
V [nm3]
Z
ρcalc [g cm−3
F(000) [e]
]
1.488
896
1.512
928
1.512
1920
1.638
2064
θ range [deg]
2.02 – 25.03
38038
3468
0.0225
3468 / 253
1.068
2.01 – 26.39
16414
4108
0.0246
4108 / 262
1.097
1.67 – 26.37
51924
8512
0.0397
8512 / 533
1.118
1.65 – 24.77
63532
7213
0.0938
7213 / 533
0.964
No. of collected reflexions
No. of independent reflexions
Rint
Data / parameters
Goof
R1, wR2 [I > 2σ(I)]a,b
R1, wR2 (all data)
0.0248, 0.0667 0.0381, 0.1027 0.0391, 0.0839 0.0379, 0.0653
0.0264, 0.0676 0.0419, 0.1050 0.0468, 0.0870 0.0662, 0.0712
0.0388, 1.2738 0.0575, 1.8977 0.0365, 4.4777 0.0339, 0.0000
0.580 / −0.181 0.519 / −0.349 0.565 / −0.269 0.348 / −0.516
c
g1, g2
−3
˚
Largest diff peak / hole [e·A
]
Structure Determination of 1 – 4
parameters. All hydrogen atoms bonded to sp2 carbon atoms
were assigned ideal positions and refined using a riding
model with Uiso constrained to 1.2 times the Ueq value of
the parent atom.
Crystallographic data (excluding structure factors) for the
structures 1 – 4 have been deposited with the Cambridge
Crystallographic Data Centre. The CCDC numbers are listed
in Table 2. Copies of the data can be obtained free of
charge from The Cambridge Crystallographic Data Centre
via www.ccdc.cam.ac.uk/data request/cif.
Crystal data are presented in Table 2. The data were col-
lected from oil-coated shock-cooled crystals. Compounds 1 –
3 were measured on a Bruker SMART-APEX diffrac-
tometer with a D8 goniometer, and 4 on a Stoe IPDS-2.
Both diffractometers were equipped with low-temperature
devices and used graphite-monochromated MoKα radia-
tion, λ = 71.073 pm [17]. The data of 1 – 3 were in-
tegrated with SAINT [18], and an empirical absorption
correction (SADABS) was applied [19]. The data collec-
tion and reduction of 4 were performed with X-ARES and
X-RED32 [20]. The structures were solved by Direct Meth-
ods (SHELXS-97) [21] and refined by full-matrix least-
squares methods against F2 (SHELXL-97) [22]. All non-
hydrogen atoms were refined with anisotropic displacement
Acknowledgements
This work was supported by the Deutsche Forschungsge-
meinschaft. The authors gratefully acknowledge support of
CHEMETALL GmbH, Frankfurt/Main and Langelsheim.
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G. Schwab et al. · 9-Bromo-10-diphenylphosphanylanthracene and its Oxidation Products
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