6394 J. Org. Chem.

1998, 63, 6394-6397

Synthesis of 2-Phenyl-1-(2-thienyl)- and Scheme 1

2-Aryl-1-(2-furyl)ethanones by the SRN1
Mechanism. Relative Reactivities of
Enolate Ions of Ketones

Marı́a T. Baumgartner, Mariana H. Gallego, and

Adriana B. Pierini*
INFIQC, Departamento de Quı́mica Orgánica, Facultad de
Ciencias Quı́micas, Universidad Nacional de Córdoba,
A.P. 4, C.C. 61, (5000) Córdoba, Argentina

Received March 17, 1998

DMSO under photostimulation.10,11 A similar behavior
The synthesis of R-aryl ketones has received much
has been observed with the enolate ions of 2-acetylnaph-
attention over the past two decades. Several arylation
thalene12 and other aromatic ketones such as 2-acetyl-
reactions have been devised with the assistance of
furan8b,11 and 2-acetylthiophene. The latter carbanion
transition metal catalysis, although each of them requires
special reagents or gives unsatisfactory yields.1 Beside has been reported to afford the substitution product only
aryl halides other reagents such as aryliodonium salts, by reaction with phenyl azosulfides,13 which are very good
aryllead, and arylbismuth reagent have been proposed electron acceptors that react spontaneously or under
for this purpose.2 Also the reaction of silyl enol ether laboratory light with different nucleophiles. The differ-
with arenediazonium salts in the presence of Pd(0) and ence in reactivity between enolate anions of aromatic and
tetraphenylborate anion gave R-aryl ketones.3 Recently aliphatic ketones toward phenyl halides in liquid am-
it has been reported that the arylation of ketone enolate monia has been attributed to the lower efficiency of the
ions with aryl bromides gave good yields of R-aryl ketones former in the photoinitiation step of the proposed mech-
by a palladium-catalyzed coupling in the presence of Tol- anism (Scheme 1).5 This situation can be overcome by
BINAP or BINAP as a ligand.4 employing other methods of initiation like solvated
The SRN1 mechanism is also an important route to electrons from alkali metals, electrochemically, favoring
achieve the synthesis of this type of compounds.5 Good the initial electron transfer at higher temperatures
percentages of substitution are usually obtained with (DMSO, rt), or performing the reaction in the presence
enolate ions of aliphatic ketones, mainly from acetone and of added nucleophiles that are less reactive than the
pinacolone. These anions react with phenyl halides enolate anion of the aromatic ketone toward phenyl
under photostimulation in liquid ammonia (-33 °C) or radicals (eq 3) but are better electron donors to initiate
in DMSO at room temperature. In DMSO substitution the chain (eq 1) (entrainment reaction).
can be achieved without photostimulation with sub- On this basis, we studied the reaction of the enolate
strates that are very good electron acceptors.6 ions of 2-acetylthiophene and 2-acetylfuran with different
Aromatic ketones behave somewhat different. For aryl halides to determine their reactivity, the initiation
example, the enolate ion of acetophenone reacts with conditions that favor the substitution reaction, and the
halobenzenes or halonaphthalenes in liquid ammonia possibility of increasing their synthetic scope. Photoini-
under irradiation only under drastic conditions.7 Het- tiation and initiation by ferrous ion were carried out.
eroarylation of the anion can be achieved in this solvent Ferrous ion (usually FeSO4 in liquid ammonia and FeCl2
either under irradiation or even in the dark with highly or FeBr2 in DMSO)14 can provide an alternative and
electrophilic substrates.8,9 On the other hand, phenyla- efficient method to initiate the reaction of carbanions
tion as well as heteroarylation of the anion is possible in with iodobenzene and other aryl halides. The relative
reactivities of the enolate ions of 2-acetylthiophene and
(1) (a) Semmelhack, M. F.; Stauffer, R. D.; Rogerson, T. D. Tetra-
hedron Lett. 1973, 4519. Semmelhack, M. F.; Chong, B. P.; Stauffer,
2-acetylfuran with respect to the enolate ions of ac-
R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, etophenone and 2-acetylnaphthalene were determined.
97, 2507. (b) Kalinin, V. N. Synthesis 1992, 413 and references therein.
(2) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P Tetrahedron
1988, 44, 3039 and references therein cited. (8) (a) Oostvee, E. A.; van der Plas, H. C. Recl. Trav. Chim. Pays-
(3) Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Perkin Trans. Bas 1979, 98, 441. (b) Nair, V.; Chamberlain, S. D. J. Am. Chem. Soc.
1 1994, 283. 1985, 107, 2183.
(4) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (9) (a) Hay, J. V.; Wolfe, J. F. J. Am. Chem. Soc. 1975, 97, 3702.
Tol-BINAP (2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl; BINAP (2,2′- Hay, V. J.; Hudlicky, T.; Wolfe, J. F. J. Am. Chem. Soc. 1975, 97, 374.
bis(diphenylphosphino)-1,1′-binaphthyl. (b) Carver, D. R.; Komin, A. P.; Hubbard, J. S.; Wolfe, J. F. J. Org.
(5) (a) Rossi, R. A.; Peñéñory, A. B.; Pierini, A. B. in The Chemistry Chem. 1981, 46, 294.
of Functional Group; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester; (10) Borosky, G. L.; Pierini, A. B.; Rossi, R. A. J. Org. Chem. 1992,
1995; Supl. D2, Chapter 24, p 1395. (b) Norris, R. K. Comprehensive 57, 247.
Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. (11) Beugelmans, R.; Bois-Choussy, M. Heterocycles 1987, 26, 1863.
4, p 451. (12) Beugelmans, R.; Bois-Choussy, M.; Tang, Q. J. Org. Chem.
(6) Scamehorn, R. G.; Bunnett, J. F. J. Org. Chem. 1977, 42, 1449. 1987, 52, 3880.
Scamehorn, R. G.; Bunnett, J. F. J. Org. Chem. 1979, 44, 2604. (13) Dell’Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron
Scamehorn, R. G.; Hardacre, J. M.; Lukanich, J. M.; Sharpe, L. R. J. 1993, 49, 235. Dell’Erba, C.; Novi, M.; Petrillo, G.; Tavani, C.
Org. Chem. 1984, 49, 4881. Phosphorus, Sulfur and Silicon 1993, 74, 409.
(7) (a) Bunnett, J. F.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1702. (14) (a) Galli, C.; Bunnett, J. F. J. Org. Chem. 1984, 49, 3041. (b)
(b) Rossi, R. A.; de Rossi, R. H.; López, A. F. J. Am. Chem. Soc. 1976, van Leeuwen, M.; Mckillop, A. J. Chem. Soc., Perkin Trans. 1 1993,
98, 1252. (c) Semmelhack, M. F.; Bargar, T. M. J. Am. Chem. Soc. 1980, 2433. (c) Galli, C.; Gentili, P. J. Chem. Soc., Perkin Trans. 2 1993,
102, 7765. 1135. (d) Murguı́a, M. C.; Rossi, R. A. Tetrahedron Lett. 1997, 38, 1355.

S0022-3263(98)00499-X CCC: $15.00 © 1998 American Chemical Society

Published on Web 08/15/1998
Notes J. Org. Chem., Vol. 63, No. 18, 1998 6395

Table 1. Reaction of Aryl Halides with the Carbanions

from 2-Acetylthiophene (1) and 2-Acetylfuran (2) in
DMSOa
Nu-, ArX, t-BuOK, % substit
expt M × 103 M × 103 M × 103 X- b prod (%)c
1d 1, 15.4 3, 5.1 20.6 3
2 1, 123.3 3, 44.8 133 6
3e 1, 69.5 3, 22.3 185 53 38f,g Compounds 6a and 6b afforded the indicated yields of
4h 1, 123.3 3, 44.9 173 53
5 2, 74.8 3, 26.4 103 11 substitution under irradiation (Table 1, expts 9 and 13).
6e 2, 74.8 3, 22.3 177 82 78g No substitution product was formed in the dark reaction
7h 2, 99.7 3, 35.7 156 88 of 6a, and the degree of substitution obtained with
8e,i 2, 74.8 3, 22.3 216 <9 compound 6b decreased to 34% under this condition
9 2, 74.8 6a, 24.0 148 72 69j (Table 1, expts 12 and 14). However, this percentage
10i 2, 74.8 6a, 27.4 154 74 42
11k 2, 74.8 6a, 27.4 162 79 33 increased to 58% by addition of FeBr2 (Table 1, expt 16).
12l 2, 74.8 6a, 27.4 157 14 Similar yields of substitution were obtained in the
13 2, 74.8 6b, 25.0 150 98 96 reactions of substrate 6c with the enolate ion 2 under
14l 2, 74.8 6b, 25.5 165 54 34 photostimulation (56%) or in the dark (63%). Added
15l,m 2, 74.8 6b, 25.0 155 <3
FeBr2 did not improved the degree of substitution in the
16n 2, 74.8 6b, 22.0 165 58
17 2, 74.8 6c, 25.9 165 81 56 dark (Table 1, expts 17, 18, and 19).
18l 2, 74.8 6c, 26.7 150 71 63 The percentage of substitution obtained in these reac-
19n 2, 74.8 6c, 26.8 144 42 tions not only decreased in the absence of irradiation but
20k 2, 74.8 6c, 25.7 147 84 46 also usually in the presence of radical or radical anion
a Photostimulated reactions (unless indicated), carried out under traps such as di-tert-butylnitroxide (DTBN) and p-DNB,
nitrogen at 40 °C. Irradiation time (180 min). b Determined respectively (Table 1, expts 8, 10, 11, 15, and 20).
potentiometrically on the basis of substrate concentration. c De- The relative reactivities of anions 1 and 2 and the
termined by GLC and the internal standard method. d Reaction
carried out in liquid ammonia. e Reaction performed in the pres-
enolate ions of acetophenone (8) and 2-acetylnaphthalene
ence of acetonate anion (M × 103 ) 68). f Benzene was detected (9) were determined in competition experiments under
but not quantified. g Traces of phenylacetone (<1%). h Dark reac- photoinitiation as well as under iron(II) initiation. The
tion in the presence of FeBr2 (40 mmol %). Reaction time (30 min). relative reactivities were estimated according to the
Temperature (25 °C). i p-Dinitrobenzene (30 mmol %). j Naphtha- approximation previously reported.15
lene was quantified (4%). k Di-tert-butylnitroxide (30 mmol %).
l Dark reaction. m p-Dinitrobenzene (60 mmol %). n Dark reaction, In the photostimulated reaction of 3 with nucleophiles
FeBr2 (80 mmol %). 8 and 9 in excess, we determined a k9/k8 ) 1.1116 (Table
2). The enolate ion of 2-acetylthiophene (1) was 0.5 times
Results less reactive than the enolate ion of acetophenone (8).
The enolate ion of 2-acetylfuran (2) was 0.8 times less
Enolate Ions of 2-Acetylthiophene (1) and 2-Acetyl-
reactive than the enolate ion of acetophenone.17
furan (2). The enolate ions 1 and 2 failed to react with
In the iron(II)-induced competition reactions the eno-
iodobenzene (3) under photoinitiation either in liquid
late ion 1 was 0.6 times less reactive than carbanion 8
ammonia or DMSO in the presence of excess t-BuOK
and the enolate anion 2 had the same reactivity as the
(Table 1, expts 1, 2, and 5, respectively). The degree of
enolate ions 8 and 9 (Table 3).
dehalogenation obtained in these reactions increased
On the basis of the present experimental evidences,
when they were performed in DMSO and in the presence
the entrainment of the photoinitiated reactions by added
of good electron donors such as the enolate ion of acetone
acetone enolate anion and the inhibition of the reactions
(entrainment reaction). Under these conditions the high-
by radical and radical anion scavengers, we propose that
est percentage of substitution products 4 (38%) and 5
the enolate anions of 2-acetylfuran and 2-acetylthiophene
(78%), from anions 1 and 2, respectively, were obtained
react with aryl halides by the SRN1 mechanism. The low
with a substrate:nucleophile:acetonate ion ratio of 1:3:3
reactivity of these anions in photoinitiated reactions with
(Table 1, expts 3 and 6).
3 and the considerable higher reactivity observed in the
presence of the enolate ion of acetone indicate that they

(15) The equation used in the relative reactivity determination of

pairs of nucleophiles vs a radical is

k1 ln([Nu1]0/[Nu1]t)
)
k2 ln([Nu2]0/[Nu2]t)
The dark reactions of anions 1 and 2 with 3, in the
presence of 40% of FeBr2, afforded 53% and 88% of where [Nu1]0 and [Nu2]0 are initial concentrations and [Nu1]t and
[Nu2]t are concentration at time t of both nucleophiles. This
substitution products, respectively (Table 1, expts 4 and equation is based on a first-order reaction of both anions with the
7). These percentages of substitution, higher than the phenyl radicals, see: Bunnett, J. F. In Investigation of Rates and
Mechanisms of Reactions, 3rd ed.; Lewis, E. S., Ed.; Wiley-
ones obtained under photostimulation, were achieved Interscience: New York, 1974; Part 1, p 159.
without the need of added nucleophiles and with the (16) (a) A k9/k8 ) 1.35 can be calculated from ref 16b. (b) Galli, C.;
advantage of no side products from their possible pho- Gentili, P.; Guarnieri, A. Gazz. Chim. Ital. 1995, 125, 409.
(17) This relative reactivity order is obtained when the enolate ions
tostimulated decomposition. 8 and 2 are present in aproximatelly a 3-fold excess with respect to
The anion 2 reacted with better electron acceptor the substrate; however when they are present at a concentration
substrates such as 1-iodonaphthalene (6a), 9-bromoan- similar to that of the substrate the relative reactivity is ca. 1.5 and
the total percentage of reaction decreases to less than 20%. This
thracene (6b), and 4-bromobenzophenone (6c) to afford dependence of the percentage of substitution with the nucleophile:
the following yields of ketones 7a-c, respectively. substrate ratio was observed only under photostimulation.
6396 J. Org. Chem., Vol. 63, No. 18, 1998 Notes

Table 2. Photostimulated Relative Reactivity of Enolate Ions of Ketones toward PhIa

substit prod (%)
rel reactivity
carbanions from Nu1:Nu2 mmol
,b % X- c PhNu1 PhNu2 av
2-acetylfuran (2) 2.8:3.0 17 5 7 0.76
vs 6.7:3.8 50 29 19 0.86
acetophenone (8) 4.4:5.7 62 27 40 0.87
k2/k8 0.83 ( 0.06
2-acetylthiophene (1) 6.2:3.8 95 50 58 0.51
vs
acetophenone (8) 4.1:5.7 81 20 58 0.47
k1/k8 0.49 ( 0.03
2-acetylnaphthalene (9) 3.0:3.0 47 29 23 1.27
vs 2.2:4.1 52 18 36 0.93
acetophenone (8) 5.1:8.7 49 22 33 1.14
k9/k8 1.11 ( 0.17
a Reactions carried out at 40 °C in 40 mL of DMSO with 1 mmol of PhI. Irradiation time 120 min. b Nu2 ) enolate anion of acetophenone.
c On the basis of substrate concentration.

Table 3. Relative Reactivity of Enolate Ions of Ketones toward PhI in the Presence of FeBr2a
substit prod (%)
rel reactivity
carbanions from Nu1:Nu2,b mmol PhNu1 PhNu2 av
2-acetylfuran (2) 6.7:4.4 64 43 0.98
vs 5.6:5.5 53 51 1.02
acetophenone (8) 4.4:6.7 40 59 1.03
k2/k8 1.01 ( 0.03
2-acetylthiophene (1) 6.6:6.3 28 46 0.57
vs
acetophenone (8) 4.5:6.7 18 45 0.59
k1/k8 0.58 ( 0.01
2-acetylnaphthalene (9) 7.4:4.9 22 16 0.91
vs 5.6:5.5c 14 12 1.15
acetophenone (8) 4.7:6.7 13 22 0.84
k9/k8 0.97 ( 0.16
a Reactions carried out at 25 °C in 40 mL of DMSO with 1 mmol of PhI. Nu2 ) enolate anion of acetophenone. Temperature (60 °C).
b c

are unable to initiate the process with this substrate. The The possibility of initiating these reactions with Fe-
electron transfer capability of enolate anions in the (II) salts is an interesting synthetic possibility. Under
initiation has been shown to roughly follow the same these conditions no special photochemical device is
order as that of the pKa of the conjugated acids of the required, and the formation of products from photochemi-
carbanions.18 Even though the pKa of the conjugated cal decomposition of the carbanions is avoided. On the
acids of carbanions 1, 2, and 9 have not been reported, other hand, the similar relative reactivity order obtained
they are expected to be lower than the pKa of acetophe- in competition experiments under light and iron(II)
none and acetone (pKa ) 24.7 and 26.5, respectively).19 initiation, previously reported with other pair of nucleo-
These facts would explain their higher reactivity toward philes,14c can be taken as an indication of the presence
more electrophilic and thus better electron acceptor of the same reaction intermediates under both methods
compounds such as 1-iodonaphthalene, 9-bromoan- of initiation.
thracene, 4-bromobenzophenone, 5-chloro-7-iodo-8-isopro-
poxyquinoline,9a and 6-iodo-9-ethylpurine.9a Experimental Section
The relative reactivities determined indicate that the
enolate ions 1 and 2 are more efficient than the enolate General Method. Irradiation was conducted in a reactor
ion of acetone in the coupling reaction of the process (eq equipped with two 400-W lamps emitting maximally at 350 nm
(Philips Model HPT, air and water refrigerated). Potentiometric
3). The enolate ions from 2-acetylfuran, 2-acetylnaph- titration of halide ions was performed with a pH meter using a
thalene, and acetophenone have a similar reactivity Ag/Ag+ electrode.
toward phenyl radicals while the carbanion from 2-acetyl- Materials. PhI, FeBr2, 4-bromobenzophenone, 9-bromoan-
thiophene is half as reactive. thracene, 1-iodonaphthalene, and t-BuOK were commercially
Comparison of the relative reactivities determined for available and used as received. DMSO was distilled under
the anions of acetophenone and 2-acetylnaphthalene vacuum and stored under molecular sieves (4 Å). Acetophenone
toward 3 with the value reported toward iodonorcarane was distilled and stored with molecular sieves (4 Å). 2-Acetylth-
iophene and 2-acetylfuran (Aldrich) were distilled. 2-Acetyl-
(k9/k8 ) 1.7)20 is another piece of evidence indicating that naphthalene (Jonhson Matthey Alfa Products) was recrystallized
phenyl radicals are less selective than norcaranyl radicals from petroleum ether.22
in their reaction toward carbanions. Similar results were Photostimulated Reaction of Enolate Ions with 3. The
obtained for the reaction of phenyl and 1-adamantyl following procedure is representative. The reactions were
radicals toward enolate ions of ketones.21 carried out in a 100 mL three-neck round-bottomed flask

(18) Bordwell, F. G.; Clemens, A. H.; Smith, D. E.; Begemann, J. J. (21) Rossi, R. A.; Pierini, A. B.; Borosky, G. L. J. Chem. Soc., Perkin
Org. Chem. 1985, 50, 1151. Trans. 2 1994, 2577.
(19) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456. (22) Perrin, D. D.; Armarego, W. L. F. Purif. Lab. Chem., 3rd ed.;
(20) Rossi, R. A.; Nazareno, M. A. J. Org. Chem. 1996, 61, 1645. Butterworth-Heinemann Ltd.: Oxford, 1994.
Notes J. Org. Chem., Vol. 63, No. 18, 1998 6397

equipped with nitrogen inlet and magnetic stirrer. To 40 mL of 189 (35.2), 165 (8.3), 95 (14.0), 38 (19.1); HRMS calcd for
dry and degassed DMSO under nitrogen were added 6.0 mmol C20H14O2 286.0994, found 286.0994.
of t-BuOK and 5.0 mmol of 2-acetylthiophene. After 15 min 3 2-(4-Benzoylphenyl)-1-(2-furyl)ethanone (7c) was isolated
(1.5 mmol) was added and the reaction mixture was irradiated by column chromatography and eluted with petroleum ether/
for 3 h. The reaction was quenched with an excess of ammonium acetone (90:10): 1H NMR (Cl3CD) δ 4.22 (s, 2H); 6.53-6.58 (dd,
nitrate and water (120 mL). The mixture was extracted twice 1H); 7.25-7.30 (dd, 1H); 7.37-7.65 (m, 6H); 7.73-7.83 (m, 4H);
with methylene chloride (40 mL), and the organic extract was 13C NMR (Cl CD) δ 45.2, 112.5, 118.0, 128.2, 129.5, 130.5, 132.1,
3
washed twice with water, dried, and quantified by GLC. The 136.0 (c), 137.7 (c), 139.0 (c), 146.9, 152.1 (c), 185.6 (c), 196.1
iodide ions in the aqueous solution were determined potentio- (c); MS (relative intensity) m/e ) 292 (0.1), 291 (0.9), 290 (5.0),
metrically. 196 (0.2), 195 (0.8), 168 (0.8), 167 (5.7), 106 (0.3), 105 (3.0), 97
The solvent was removed under reduced pressure. The (0.6), 96 (4.6), 95 (100), 78 (0.7), 77 (8.7), 76 (0.4), 53 (0.8), 52
residue after column chromatography on silica gel and eluted (0.7), 51 (8.7); HRMS calcd for C19H14O3 290.0943, found
with petroleum ether/diethyl ether (90:10) gave a mixture of 290.0939.
2-acetylthiophene and 2-phenyl-1-(2-thienyl)ethanone. This
Fe(II)-Induced Reaction of 2 with 3. To 30 mL of dry and
mixture was distilled under reduced pressure in the Kügelrohr
degassed DMSO under nitrogen were added 6.0 mmol of t-BuOK,
apparatus to give 2-phenyl-1-(2-thienyl)ethanone (4): 1H
5.0 mmol of 2-acetylthiophene, and 0.6 mmol of FeBr2. After a
NMR3 (Cl3CD) δ 4.1 (s, 2H); 7.1 (dd, 1H, J ) 3.8, 4.9); 7.2-7.3
few minutes 3 (1.5 mmol) was added. The reaction was
(m, 5H); 7.6 (dd, 1H, J ) 1.0, 4.9); 7.7 (dd, 1H, J ) 1.0, 3.8).
quenched after 30 min.
1-(2-Furyl)-2-Phenylethanone (5) was isolated by column
chromatography and eluted with petroleum ether/dietyl ether Competition Reactions of Two Different Enolates Ions
(90:10). The liquid isolated was distilled in the Kügelrohr toward 3. To estimate the relative reactivities of these nucleo-
apparatus: 1H NMR3 (Cl3CD) δ 4.05 (s, 2H); 6.45 (dd, 1H, J ) philes, photostimulated reaction and FeBr2 induced reactions
3.5, 1.8); 7.1 (dd, 1H, J ) 3.5, 0.7); 7.15-7.25 (m, 5H); 7.5 (dd, were carried out. In 40 mL of dry and degassed DMSO under
1H, J ) 1.8, 0.8). nitrogen, 12 mmol of t-BuOK, 4 mmol of acetophenone, and 6
1-(2-Furyl)-2-(1-naphthyl)ethanone (7a) was isolated by mmol of 2-acetylfuran were added. Then 1 mmol of FeBr2 was
column chromatography and eluted with petroleum ether/diethyl added. After a few minutes, 1 mmol of 3 was added. After a
ether (90:10): 1H NMR23 (Cl3CD) δ 4.58 (s, 2H), 6.48-6.55 (dd, reaction time of 30 min (FeBr2-induced reaction) or 3 h (under
1H); 7.19-7.24 (dd, 1H); 7.39-7.61 (m, 5H); 7.72-7.89 (m, 2H); photostimulation), the reaction was quenched by addition of
7.94-7.85 (m, 1H); 13C NMR (Cl3CD) δ 42.9, 112.7, 117.9, 124.0, ammonium nitrate in excess.
125.4, 125.7, 126.3, 127.9, 128.2, 128.7, 130.7 (c), 132.39 (c), 133.9
(c), 146.0, 152.8 (c), 186.5 (c); MS (relative intensity) m/e 238 Acknowledgment. This work was supported in part
(0.7), 237 (5.2), 236 (29.9), 143 (0.7), 142 (11.3), 141 (86.1), 115 by the Consejo Nacional de Investigaciones Cientı́ficas
(31.1), 97 (0.3), 96 (2.7), 95 (47.3), 89 (3), 63 (6.2), 51 (8.3), 40
(3.4), 39 (100).
y Técnicas (CONICET), CONICOR, SECyT, and Antor-
2-(9-Anthryl)-1-(2-furyl)ethanone (7b) was isolated by chas Fundation Argentina. M.H.G. acknowledges receipt
column chromatography and eluted with petroleum ether/diethyl of a fellowship from CONICET.
ether (90:10): mp 172-173.5 °C; 1H NMR (Cl3CD) δ 5.16 (s, 2H);
6.49-6.55 (dd, 1H); 7.20-7.25 (dd, 1H); 7.33-7.56 (m, 5H); 7.56- Supporting Information Available: 1H NMR spectra for
7.70 (m, 1H); 7.69-7.80 (m, 4H); 13C NMR (Cl3CD) δ 38.5, 112.6, compounds 7b and 7c (2 pages). This material is contained
117.8, 124.1, 124.8, 126.1, 127.4, 129.0, 130.6 (c), 131.6 (c), 146.3, in libraries on microfiche, immediately follows this article in
152.2 (c), 186.2 (c); MS (relative intensity) m/e ) 288 (0.4), 287 the microfilm version of the journal, and can be ordered from
(3.4), 286 (18.5), 193 (1.3), 192 (16.5), 191 (100.0), 190 (13.4), the ACS; see any current masthead page for ordering
information.
(23) Duval, O.; Mavoungou Gomès, L. Bull. Soc. Chim. Fr. 1987,
131. JO9804994