Sodium diarylbismuthide as a reagent for the bismuthanation of reactive arenes. Application to the synthesis of mixed triarylbismuthanes bearing a substituent group incompatible with Grignard and organolithium reagents

Article abstract of DOI:10.1021/om9701377

Several mixed triarylbismuthanes bearing an electron-withdrawing functionality, such as the nitro, carbonyl, or ester group, which are inaccessible by the conventional methods based on organometallic reagents such as Grignard and organolithium compounds, are synthesized in low to acceptable yields by the reaction of in situ generated sodium diarylbismuthide with iodoarenes or arenediazonium tetrafluoroborates.

Full text of DOI:10.1021/om9701377

Organometallics 1997, 16, 3565-3568
3565
Sod iu m Dia r ylbism u th id e a s a Rea gen t for th e
Bism u th a n a tion of Rea ctive Ar en es. Ap p lica tion to th e
Syn th esis of Mixed Tr ia r ylbism u th a n es Bea r in g a
Su bstitu en t Gr ou p In com p a tible w ith Gr ign a r d a n d
Or ga n olith iu m Rea gen ts
Md. Mizanur Rahman, Yoshihiro Matano, and Hitomi Suzuki*
Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa,
Sakyo-ku, Kyoto 606, J apan
Received February 24, 1997X
Sch em e 1
Summary: Several mixed triarylbismuthanes bearing an
electron-withdrawing functionality, such as the nitro,
carbonyl, or ester group, which are inaccessible by the
conventional methods based on organometallic reagents
such as Grignard and organolithium compounds, are
synthesized in low to acceptable yields by the reaction
of in situ generated sodium diarylbismuthide with
iodoarenes or arenediazonium tetrafluoroborates.
In tr od u ction
naphthalenide produced, smoothly, the corresponding
bismuthide anion as a deep green tetrahydrofuran
(THF) solution at low temperature. Herein, we report
a new and reliable method for the preparation of the
title triarylbismuthanes.
In connection with the ongoing program in our
laboratory, we needed some unsymmetrical triarylbis-
muthanes bearing an electron-withdrawing functional-
ity, such as the nitro, carbonyl, or ester group. The most
general method for the synthesis of unsymmetrical
triarylbismuthanes is the reaction of an aryl Grignard
or an aryllithium reagent with an arylbismuth dihalide
or a diarylbismuth halide.1 These arylbismuth halides
are in turn obtained by the ligand exchange reaction
between a symmetrical triarylbismuthane and a bis-
muth(III) halide, choice of the major product depending
on the ratio of the respective reagents (Scheme 1).1,2 In
any case, however, these organometallic approaches are
not applicable for our present purpose because of their
incompatibility with the unsaturated polar functions,
such as the nitro, carbonyl, and ester group.
An alternative possible choice may be the bismutha-
nation of haloarenes with sodium diarylbismuthide,
which has long been known and can be generated by
the reaction between diarylbismuth halides and sodium
metal in liquid ammonia.3 To our knowledge, however,
this type of reaction has not been previously examined
as a means for the preparation of unsymmetrical
triarylbismuthanes. In order to circumvent the use of
sodium metal and liquid ammonia, we sought to find
an alternative method for the generation of the diaryl-
bismuthide anion and found that the combination of the
diarylbismuth trifluoromethanesulfonate-hexameth-
ylphosphoric triamide (HMPA) complex4 and sodium
Resu lts a n d Discu ssion
Bis(4-methylphenyl)bismuth
trifluoromethane-
sulfonate-HMPA complex (2), prepared from tris(4-
methylphenyl)bismuthane (1) according to the reported
procedure,4 was treated with sodium naphthalenide in
THF at -78 °C to generate sodium bis(4-methylphenyl)-
bismuthide (3), which was subsequently reacted with
1-iodonaphthalene (4a ) or 9-iodophenanthrene (4b) to
give the corresponding mixed triarylbismuthanes (6a
and b) in 46% and 52% yields, respectively (Scheme 2).
However, hindered 9-iodoanthracene (4c) failed to react
in the expected manner. Mixed triarylbismuthanes
6a ,b were also obtainable by the reaction of a diaryl-
bismuth halide and an aryllithium. Thus, when treated
with 1-naphthyllithium (9a ) and 9-phenanthryllithium
(9b), bis(4-methylphenyl)bismuth bromide (8) gave the
corresponding tertiary bismuthanes 6a and 6b in 82%
and 52% yields, respectively. By this procedure, 9-an-
thrylbis(4-methylphenyl)bismuthane (6c) was also ac-
cessible in 51% yield.
When the above methodology based on sodium dia-
rylbismuthide was extended to the reaction with ha-
lonitroarenes, to our disappointment a complicated
mixture of products resulted and no tertiary bismuth-
anes containing the nitrophenyl moiety could be isolated
in our hands.
Next, we turned out attention to the arenediazonium
salt, a more reactive aryl donor as compared with
iodoarene. Barton and co-workers have previously
reported that the copper-induced decomposition of 4-ni-
trobenzenediazonium tetrafluoroborate (5d ) in dimeth-
* Author to whom correspondence should be addressed. E-mail:
suzuki@kuchem.kyoto-u.ac.jp.
X Abstract published in Advance ACS Abstracts, J uly 1, 1997.
(1) For a review, see: Freedman, L. D.; Doak, G. O. Chem. Rev. 1982,
82, 15. Also refer to: Wiber, M. Gmelin Handbook of Inorganic
Chemistry; Springer-Verlag: Berlin, 1978.
(2) For example, see: Challenger, F.; Allpress, C. F. J . Chem. Soc.
1915, 107, 16.
(3) (a) Gilman, H.; Yablunky, H. L. J . Am. Chem. Soc. 1941, 63,
212. (b) Kaufmann, F.; Steinseifer, F.; Klas, N. Chem. Ber. 1985, 118,
1039. For the bismutanation using sodium dimethylbismuthide, see:
(b) Wieber, M.; Saucer, I. Z. Naturforsch., B 1985, 40, 1476. (C) Wieber,
M.; Rudolph, K. Z. Naturforsch., B 1988, 3, 739.
(4) Matano, Y.; Miyamatsu, T.; Suzuki, H. Organometallics 1996,
15, 1951.
S0276-7333(97)00137-4 CCC: $14.00 © 1997 American Chemical Society

3566 Organometallics, Vol. 16, No. 15, 1997
Notes
Sch em e 2
Sch em e 3
ylformamide (DMF) in the presence of bismuthane 1
gave bis(4-methylphenyl)(4-nitrophenyl)bismuthane (6d)
and (4-methylphenyl)bis(4-nitrophenyl)bismuthane (7d )
in 12% and 15% yields, respectively.5 However, the
thermal decomposition of arenediazonium salts occurs
in a homolytic way to give a complicated mixture of
products, from which each component can usually be
obtained with difficulty. Hence, we examined the
reaction of sodium diarylbismuthide 3 with diazonium
salt 5d in THF at -78 °C and obtained the expected
products 6d and 7d in 15% and 6% isolated yields,
respectively (Scheme 2). In this reaction, the composi-
tion of the product mixture was simple and compounds
6d and 7d were easily isolated by column chromatog-
raphy on silica gel. Other products were those arising
from simple decomposition of the starting materials.
Similar reaction of 3 with diazonium salts 5e and 5f
in THF at -78 °C afforded bismuthanes 6e and 6f, both
in about 10% yield. Attempts to improve the yield of
bismuthanes 6 by using the iodonium salt 106 in place
of diazonium salt 5 met with failure. The reaction of
mixed triarylbismuthanes 6b and 6c with sulfuryl
chloride in dichloromethane at low temperature afforded
the corresponding dichlorides 11 and 12 in 90% and 88%
yields, respectively (Scheme 3).
carbonyl, or ester group on an aromatic ring, which are
inaccessible by the known methodologies based on
common organometallic reagents such as Grignard and
organolithium compounds. Although the yields are
unsatisfactory, this method seems to provide the only
reliable direct route available at the present time to this
type of mixed triarylbismuthane.
In summary, we have developed a new method for the
synthesis of mixed triarylbismuthanes having a nitro,
Exp er im en ta l Section
(5) Barton, D. H. R.; Bhatnagar, N. Y.; Finet, J .-P.; Motherwell, W.
B. Tetrahedron 1986, 42, 3111.
Gen er a l Com m en ts. All reactions were carried out under
(6) Kazmierczak, P.; Skulski, L. Synthesis 1995, 1027.
argon. Melting points were measured on a Yanagimoto hot-

Notes
Organometallics, Vol. 16, No. 15, 1997 3567
stage apparatus and are uncorrected. Tetrahydrofuran (THF)
and diethyl ether were distilled from benzophenone ketyl
under argon before use. Bismuth(III) bromide and sulfuryl
chloride were used as commercially received. n-Butyllithium
was titrated against diphenylacetic acid.7 The aromatic iodo
compounds (4a -c)8 and diazonium compounds (5d ,f)9 were
prepared according to the reported procedures. Thin layer
chromatography (TLC) was performed by using Merck pre-
coated silica gel sheets, 60F-254. Silica gel (Wakogel) of size
200 mesh was used for column chromatography. 1H NMR (200
MHz) spectra were recorded on a Varian Gemini-200 spec-
trometer for CDCl3 solutions, with tetramethylsilane (TMS)
as an internal standard. IR spectra were recorded on a
Shimadzu FTIR-8100S spectrophotometer, and only prominent
peaks below 2000 cm-1 are recorded. Electron impact mass
spectra (EIMS) were obtained at 70 eV on a Shimadzu GCMS-
QP2000A spectrometer, and fast atom bombardment mass
spectra (FABMS) were obtained on a J EOL J MS-HS110
spectrometer using 3-nitrobenzyl alcohol as a matrix. Elemen-
tal analyses were performed at Microanalytical Laboratory of
Kyoto University.
Rea ction of Bis(4-m eth ylp h en yl)bism u th Br om id e (8)
w ith Ar yllith iu m s 9a -c. Typ ica l P r oced u r e. 9-Anthryl-
lithium (9c) was generated by stirring n-butyllithium (1.43
M, 0.77 mL, 1.1 mmol) and 9-bromoanthracene (0.26 g, 1.0
mmol) in diethyl ether (10 mL) for 2 h at room temperature.
To the solution of 9c thus obtained was added with vigorous
stirring at -78 °C a suspension of bis(4-methylphenyl)bismuth
bromide (8), generated from tris(4-methylphenyl)bismuthane
(0.32 g, 0.67 mmol) and bismuth(III) bromide (0.15 g, 0.33
mmol) in diethyl ether (10 mL), and the resulting mixture was
allowed to gradually warm to room temperature. After the
reaction mixture was stirred at room temperature for 1 h, the
mixture was worked up as usual and the product was
recrystallized from methanol to afford bis(4-methylphenyl)(9-
anthryl)bismuthane (6c) as crystals (0.29 g, 51%). Mp: 148-
151 °C. 1H NMR: δ 2.31 (s, 6H), 7.10 (d, J ) 8 Hz, 4H), 7.1-
7.3 (m, 4H), 7.70 (d, J ) 8 Hz, 4H), 8.0-8.1 (m, 2H), 8.3-8.4
(m, 2H), 8.50 (s, 1H). FABMS (m/ z): 569 (M+ + 1), 476 (M+
- tolyl - H), 300 (M+ - tolyl - anthryl), 391 (M+ - anthryl),
386 (M+ - 2 tolyl), 268, 209. IR (KBr): 1486, 1445, 1385, 1310,
1262, 1010, 885, 790, 727 cm-1. Anal. Calcd for C28H23Bi: C,
59.16; H, 4.08. Found: C, 58.71; H, 4.07.
Rea ction of Sod iu m Bis(4-m eth ylp h en yl)bism u th id e
3 w ith Iod oa r en es 4a ,b. Gen er a l P r oced u r e. Bis(4-
methylphenyl)bismuth trifluoromethanesulfonate-HMPA com-
plex 2 was prepared by stirring tris(4-methylphenyl)bismuth-
ane (1; 0.48 g, 1.0 mmol), (trimethylsily)trifluomethanesulfonate
(0.19 mL, 1.0 mmol), methanol (0.5 mL), and HMPA (0.35 mL,
2.0 mmol) in dichloromethane (5 mL) for 2 h at room temper-
ature. Removal of the volatiles under reduced pressure left
complex 2 as a colorless solid residue, which was dissolved in
THF and cooled to -78 °C. Then a solution of sodium
naphthalenide, prepared from sodium metal (0.07 g, 3 mmol)
and naphthalene (0.41 g, 3.2 mmol) in THF (8 mL) at 0 °C,
was added dropwise and stirred for 5 min to generate bis-
muthide 3. To the resulting deep green solution, iodo com-
pound 4 was added in one portion with vigorous stirring at
-78 °C, and the mixture was allowed to gradually warm to
room temperature over 45 min. After the reaction mixture
was stirred for an additional 1 h at room temperature,
saturated aqueous ammonium chloride was slowly added to
the reaction mixture. The organic phase was separated and
filtered through a Celite bed. The aqueous phase was ex-
tracted with benzene (5 mL × 3), and the extract was washed
with brine (15 mL × 2). The combined organic phase was dried
over anhydrous magnesium sulfate and evaporated in vacuo
to leave an oily residue, which was chromatographed on silica
gel or recrystallized from methanol to give 6 as pale yellow
crystals.
Bis(4-methylphenyl)(1-naphthyl)bismuthane (6a ) and bis-
(4-methylphenyl)(9-phenanthryl)bismuthane (6b) were pre-
pared similarly from the corresponding iodoarenes 4a and 4b
in 80% and 51% yields, respectively.
Rea ction of Sod iu m Bis(4-m eth ylp h en yl)bism u th id e
(3) w ith Ar en ed ia zon iu m Tetr a flu or obor a tes 5d ,f. Typ i-
ca l P r oced u r e. To a solution of diarylbismuth triflate-
HMPA complex 2 (0.90 g, 1.0 mmol) in THF (5 mL) was added
dropwise at -78 °C a solution of sodium naphthalenide,
prepared from sodium metal (0.07 g, 3.0 mmol) and naphtha-
lene (0.41 g, 3.2 mmol) in THF (8 mL), and the resulting
mixture was stirred for 5 min. 4-Nitrophenyldiazonium tet-
rafluoroborate (5d ; 0.24 g, 1.0 mmol) was added portionwise
to the stirred bismuthide solution at -78 °C and then allowed
to warm to room temperature over 45 min. After the reaction
mixture was stirred for an additional 1 h at room temperature,
the mixture was worked up as usual to afford an oily residue,
which was passed through a silica gel column using hexane-
ethyl acetate (10:1) as the solvent to elute compounds 6d and
7d in this order in 15% and 5% yields, respectively.
Bis(4-m eth ylp h en yl)(4-n itr op h en yl)bism u th a n e (6d ).
Mp: 92-94 °C (lit.5,11 129-132 °C). 1H NMR: δ 2.32 (s, 6H),
7.24 (d, J ) 8.0 Hz, 4H), 7.60 (d, J ) 8.0 Hz, 4H), 7.90 (d, J )
8.0 Hz, 2H), 8.12 (d, J ) 8.0 Hz, 2H). FABMS (m/ z): 422
(M+ - tolyl), 391 (M+ - C6H4NO2), 300 (M+ - tolyl - C6H4-
NO2), 209. Anal. Calcd for C20H18BiNO2: C, 46.79; H, 3.53;
N, 2.73. Found: C, 46.19; H, 3.40; N, 2.72.
Bis(4-m et h ylp h en yl)(1-n a p h t h yl)b ism u t h a n e
(6a ).
Yield: 46%. Mp: 133-134 °C (lit.7 129-130 °C). 1H NMR:
δ 2.31 (s, 6H), 7.17 (d, J ) 8 Hz, 4H), 7.60 (d, J ) 8 Hz, 4H),
(4-Meth ylp h en yl)bis(4-n itr op h en yl)bism u th a n e (7d ).
Mp: 150-153 °C (lit.5 145-149 °C). 1H NMR: δ 2.36 (s, 3H),
7.30 (d, J ) 8.0 Hz, 2H), 7.60 (d, J ) 8.0 Hz, 2H), 7.90 (d, J )
8.0 Hz, 4H), 8.19 (d, J ) 8.0 Hz, 4H). FABMS (m/ z): 453
(M+ - tolyl), 422 (M+ - C6H4NO2), 331 (M+ - tolyl - C6H4-
7.3-7.5 (m, 3H), 7.8-8.0 (m, 4H). EIMS (m/ z): 426 (M+
-
tolyl - H), 391 (M+ - naphthyl), 336 (M+ - 2 tolyl), 300 (M+
- tolyl - naphthyl), 209. IR (KBr): 1485, 1383, 1184, 1009,
790, 769 cm-1. Anal. Calcd for C24H21Bi: C, 55.60; H, 4.08.
Found: C, 55.44; H, 4.04.
NO2), 300 (M+ - 2 C6H4NO2), 209. Anal. Calcd for C19H15
-
BiN2O4: C, 41.92; H, 2.78; N, 5.15. Found: C, 41.83; H, 2.81;
N, 5.14.
Mixed tertiary bismuthanes 6e and 6f were prepared
similarly from the corresponding arenediazonium salts 5e and
5f in 10% and 11% yields, respectively.
Bis(4-m eth ylp h en yl)(9-p h en a n th r yl)bism u th a n e (6b).
Yield: 52%. Mp: 165-170 °C. 1H NMR: δ 2.32 (s, 6H), 7.18
(d, J ) 8 Hz, 4H), 7.5-7.6 (m, 5H), 7.65 (d, J ) 8 Hz, 4H),
8.0-8.1 (m, 1H), 8.28 (s, 1 H), 8.7-8.8 (m, 2H). FABMS (m/
z): 569 (M+ + 1), 477 (M+ - tolyl), 300 (M+ - tolyl -
phenanthryl), 391 (M+ - phenanthryl), 386 (M+ - 2 tolyl), 286,
Bis(4-m et h ylp h en yl)(4-ca r b et h oxyp h en yl)b ism u t h -
a n e (6e). Pale yellow oil. 1H NMR: δ 2.32 (s, 6 H), 1.37 (t, J
) 6.9 Hz, 3H), 4.35 (q, J ) 6.9 Hz, 2H), 7.20 (d, J ) 7.6 Hz, 4
H), 7.61 (d, J ) 7.6 Hz, 4H), 7.81 (d, J ) 8.2 Hz, 2H), 8.01 (d,
209. IR (KBr): 1485, 1442, 1051, 1008, 794, 744, 715 cm-1
.
Anal. Calcd for C28H23Bi: C, 59.16; H, 4.08. Found: C, 59.11;
H, 4.06.
J ) 8.2 Hz, 2H). FABMS (m/ z): 541 (M+ + 1), 449 (M+
-
(7) Kofron, W. G.; Baclawski, L. J . Org. Chem. 1976, 41, 1879.
(8) Suzuki, H.; Kondo, A.; Inouye, M.; Ogawa, T. Synthesis 1986,
(11) Reference 5 reported that 1H NMR (CDCl3) absorptions of the
aromatic protons of compounds 6d and 7d appeared as multiplets at
δ 8.14-7.39 and 8.17-7.39, respectively. However, these compounds
were found to show four sets of well-separated doublets in the aromatic
proton region. Contrary to the original report, a small difference in δ
values of the methyl protons of these compounds was observed; the
reported value is δ 2.35 for both compounds.
121.
(9) Flood, D. T. Organic Syntheses; Wiley: New York, 1943, Collect.
Vol. II, p 295.
(10) Gilman, H.; Yablunky, H. L. J . Am. Chem. Soc. 1941, 63,
207.

3568 Organometallics, Vol. 16, No. 15, 1997
Additions and Corrections
tolyl), 391 (M+ - C6H4CO2Et), 300 (M+ - tolyl - C6H4CO2Et),
209, 149. IR (neat): 1715 (CdO), 1584, 1387, 1281, 1103, 795,
. Anal. Calcd for C23H23BiO2: C, 51.12; H, 4.29.
Found: C, 51.82; H, 4.33.
(s, 6H), 7.57 (d, J ) 8.2 Hz, 4H), 7.6-7.8 (m, 5H), 8.0-8.1 (m,
1H), 8.25 (s, 1H), 8.65 (d, J ) 8.2 Hz, 4H), 8.7-8.8 (m, 2H).
FABMS (m/ z): 603 (M+ - Cl), 391 (M+ - 2Cl - phenanthryl),
443, 268, 209. Anal. Calcd for C28H23BiCl2: C, 52.60; H, 3.63.
Found: C, 52.23; H, 3.53.
752 cm-1
(4-Acetylp h en yl)bis(4-m eth ylp h en yl)bism u th a n e (6f).
Colorless crystals. Mp: 101-104 °C. 1H NMR: δ 2.32 (s, 6H),
2.56 (s, 3H), 7.21 (d, J ) 7.6 Hz, 4H), 7.61 (d, J ) 7.6 Hz, 4H),
7.83 (d, J ) 6.0 Hz, 2 H), 7.92 (d, J ) 6.0 Hz, 2H). FABMS
(m/ z): 511 (M+ + 1), 419 (M+ - tolyl), 391 (M+ - C6H4COMe),
300 (M+ - tolyl - C6H4COMe), 209. IR (KBr): 1684 (CdO),
1576, 1485, 1385, 1269, 1184, 1007, 953, 797 cm-1. Anal. Calcd
for C22H21BiO: C, 51.77; H, 4.15. Found: C, 51.70; H, 4.15.
Rea ction of Ar ylbis(4-m eth ylp h en yl)bism u th a n es 6b,c
w ith Su lfu r yl Ch lor id e. Typ ica l P r oced u r e. To a dichlo-
romethane (10 mL) solution of bismuthane 6b (0.30 g, 0.44
mmol) was added sulfuryl chloride (0.47 µL, 0.48 mmol) at -78
°C. As the mixture was warmed gradually to room tempera-
ture, the color of the reaction mixture turned yellow. After 1
h, the solvent was removed under reduced pressure to leave
dichloride 11 as a yellow solid, which was purified by recrys-
tallization from a mixture of dichloromethane and hexane.
Bis(4-m eth ylp h en yl)(1-p h en a n th r yl)bism u th Dich lo-
r id e (11). Yield: 90%. Mp: 145-147 °C. 1H NMR: δ 2.49
(9-An th r yl)bis(4-m eth ylph en yl)bism u th Dich lor ide (12).
Yield: 88%. Mp: 170-173 °C. 1H NMR: δ 2.49 (s, 6H), 7.4-
7.5 (m, 4H), 7.54 (d, J ) 8.5 Hz, 4H), 8.0-8.1 (2H, m), 8.3-
8.4 (m, 2H), 8.62 (s, 1H), 8.65 (d, J ) 8.5 Hz, 4H). FABMS
(m/ z): 603 (M+ - Cl), 476 (M+ - tolyl - H), 391 (M+
-
anthryl), 268, 212, 209. IR (KBr): 1522, 1473, 1446, 1385,
1266, 1248, 1183, 997, 899, 795, 727 cm-1. Anal. Calcd for
C28H23BiCl2: C, 52.60; H, 3.63. Found: C, 52.43; H, 3.50.
Ack n ow led gm en t. We acknowledge support of this
work by a Grant-in-Aid for Scientific Research (Grant
No. 05236101) from the Ministry of Education, Science,
Sports, and Culture of J apan. M.M.R. thanks the same
for the Fellowship.
OM9701377
Additions and Corrections
1996, Volume 15
Tetsu o Oh ta , Yoich i Ton om u r a , Kyok o Noza k i,
Hid em a sa Ta k a ya , a n d Ka zu sh i Ma sh im a *: An
Anionic Dinuclear BINAP-Ruthenium(II) Complex:
Crystal Structure of [NH2Et2][{RuCl((R)-p-MeO-BI-
NAP)}2(µ-Cl)3] and Its Use in Asymmetric Hydrogena-
tion.
Pages 1522-1523. An improper computer operation
caused wrong calculations of bond distances and angles
of complex (R)-2. Selected bond lengths (Å) and angles
(deg) in the caption to Figure 1 are corrected as
follows: Ru-Cl(1) ) 2.437(3), Ru-Cl(2) ) 2.423(3), Ru-
Cl(3) ) 2.493(3), Ru-Cl(3*) ) 2.518(3), Ru-P(1) )
2.271(3), Ru-P(2) ) 2.269(3); Cl(1)-Ru-Cl(2) ) 163.9(1),
Cl(1)-Ru-Cl(3) ) 79.8(1), Cl(1)-Ru-Cl(3*) ) 79.3(1),
Cl(2)-Ru-Cl(3) ) 87.6(1), Cl(2)-Ru-Cl(3*) ) 88.7(1),
Cl(3)-Ru-Cl(3*) ) 80.5(1), Cl(1)-Ru-P(1) ) 96.0(1),
Cl(1)-Ru-P(2) ) 103.5(1), Cl(2)-Ru-P(1) ) 94.8(1),
Cl(2)-Ru-P(2) ) 88.0(1), Cl(3)-Ru-P(1) ) 94.0(1),
Cl(3)-Ru-P(2) ) 173.0(1), Cl(3*)-Ru-P(1) ) 173.3(1),
Cl(3*)-Ru-P(2) ) 94.0(1), P(1)-Ru-P(2) ) 91.8(1).
The dihedral angle between the two naphthyl planes of
2 was 70.7°.
Su p p or tin g In for m a tion Ava ila ble: Corrected tables for
the crystallographic study of compound (R)-2 (21 pages).
Ordering information is given on any current masthead page.
OM970421Y