A novel synthesis of (β-organochalcogenyl)allyl phenyl sulfoxides via regioselective hydrochalcogenation reaction of 1,2-allenyl sulfoxides

Article abstract of DOI:10.1055/s-2005-869958

(β-Organochalcogenyl)allyl phenyl sulfoxides 2 were prepared by treatment of allenyl sulfoxides 1 with sodium organyl chalcogenolates in good yields. The reaction was regioselective, giving exclusively one isomer in all cases. The applications of (β-pheny

Full text of DOI:10.1055/s-2005-869958

PAPER
2171
A Novel Synthesis of (b-Organochalcogenyl)allyl Phenyl Sulfoxides via
Regioselective Hydrochalcogenation Reaction of 1,2-Allenyl Sulfoxides
S
ynthesis of (b-
h
O
rganochalc
i
ogenyl
m
)allyl Phenyl Sulfox
e
ides ng Wu,a Ruwei Shen,a Lianjun Ren,a Xian Huang*a,b
a
Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. China
Fax +86(571)88807077; E-mail: huangx@mail.hz.zj.cn
b
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,
Shanghai 200032, P. R. China
Received 27 January 2005; revised 10 March 2005
We started our investigations with the hydrotelluration re-
action of 1,2-allenyl sulfoxides 1a. When allenyl sulfox-
ide 1a was added to an ethanol solution of sodium
phenyltellurolate, prepared by reduction of diphenyl ditel-
Abstract: (b-Organochalcogenyl)allyl phenyl sulfoxides 2 were
prepared by treatment of allenyl sulfoxides 1 with sodium organyl
chalcogenolates in good yields. The reaction was regioselective,
giving exclusively one isomer in all cases. The applications of (b-
phenyltelluro)allyl phenyl sulfoxide 2d and (b-organosulfanyl)allyl luride with sodium borohydride at room temperature, to
phenyl sulfoxide 2m in organic synthesis were also described.
our delight, the (b-phenyltelluro)allyl phenyl sulfoxide 2a
was formed in 80% yield with total regioselectivity
(Scheme 1, Table 1, entry 1). Then, a series of allenyl
sulfoxides11 were prepared to study such a reaction. As
shown in Table 1, the substrates can be mono- (entry 1),
di- (entry 2) and trisubstituted (entries 3, 4) allenyl sulfox-
ides. With these results in mind, the similar procedure was
used for the synthesis of (b-organoselanyl) and (b-organo-
sulfanyl)allyl phenyl sulfoxides (Scheme 1).
Key words: allenyl sulfoxide, hydrochalcogenation, regioselectiv-
ity
Allyl sulfoxides are versatile and valuable building blocks
in organic synthesis, as shown by their remarkable utility
in the synthesis of a variety of functionalized compounds1
and natural products.2 b-Functionalized allyl sulfoxides3
are also class of compounds with significant synthetic po-
tential. Hence, efficient and convenient methods for the
synthesis of such compounds are still in demand and their
goal is a challenge.
(R4Y)2 NaBH4
+
R4YNa
EtOH
O
R3
O
R1
R1
SPh
R4YNa
EtOH
r.t., 5 min
SPh
In the last few decades, there has been remarkable interest
in the synthesis of vinylic chalcogenides and their synthet-
ic applications.4 Considering the well-known chemical re-
activities of vinylic chalcogenides, b-organochalcogenyl
substituted allyl sulfoxides, which combine the unit of vi-
nylic chalcogenides and allyl sulfoxides into one mole-
cule, will be intermediates of great synthetic potential.
Recently, we5 and others6–8 have reported the regio- and
stereoselective hydrochalcogenation reaction of electron-
deficient carbon–carbon triple bond to prepare several
functionalized vinylic chalcogenides. Another class of
compounds that attracted our interest is the electron-defi-
cient 1,2-dienes, which have been found to have high and
unique reactivity.9,10 Usually, one of the two carbon–car-
bon double bonds can be selectively reacted to give vinyl-
ic products via delicately tuning the steric and electronic
factors. Thus, hydrochalcogenation of electron-deficient
allene would be one of the most efficient ways to prepare
b-organochalcogenyl substituted allyl compounds. As a
part of ongoing study of this area, in this paper we wish to
disclose our recent results on the corresponding hydro-
chalcogenation reaction of allenyl sulfoxides.
YR4
R2
R3
R2
1
2
Scheme 1
The results are summarized in Table 1 (entries 5–16).
These reactions showed exclusive regioselectivity, and
only one regioisomer (2e–p) was obtained. For the mono-,
di-, or trisubstituted allenyl sulfoxides, yields of (b-orga-
noselanyl) (entries 5–12) and (b-organosulfanyl)allyl (en-
tries 13–16) phenyl sulfoxides were very high.
The mechanism for the current regioselective hydrochal-
cogenation reaction is believed to be a nucleophilic conju-
gate addition of RY– to allenyl sulfoxides at the b-position
to afford an allyl carbanion stabilized by the sulfoxide
group.
(b-Organochalcogenyl)allyl phenyl sulfoxides 2 are use-
ful intermediates and undergo many transformations in
organic chemistry. For example, when compound 2d was
treated with alkyne using PdCl2/CuI as the catalyst, the b-
alkynyl allyl sulfoxide 3 was obtained in moderate yields
(Scheme 2). And compound 2m can be easily oxidized to
2,3-bis(phenylsulfonyl)prop-1-ene (4)12 by MCPBA in
CH2Cl2 at room temperature (Scheme 3). Compound 3
has many valuable transformation in organic synthesis,
such as a-alkylation reaction,1b,13 1,3-rearrangement,14
1,3-dipolar cycloaddition,15 etc.16
SYNTHESIS 2005, No. 13, pp 2171–2175
x
x.
x
x
.
2
0
0
5
Advanced online publication: 24.06.2005
DOI: 10.1055/s-2005-869958; Art ID: F02105SS
© Georg Thieme Verlag Stuttgart · New York

2172
Z. Wu et al.
PAPER
Table 1 (b-Organochalcogenyl)allyl Phenyl Sulfoxides Prepared
Entry
1
R1
H
R2
H
R3
H
R4Y
Yields (%)a
Products
C6H5Te
C6H5Te
C6H5Te
C6H5Te
C6H5Se
n-C4H9Se
C6H5Se
n-C4H9Se
C6H5Se
n-C4H9Se
C6H5Se
n-C4H9Se
C6H5S
80
79
81
75
83
82
81
80
84
82
83
83
84
79
80
81
2a
2b
2c
2d
2e
2f
2
H
H
C6H5
H
3
-(CH2)5-
4
CH3
H
CH3
H
H
5
H
6
H
H
H
7
H
H
C6H5
C6H5
H
2g
2h
2i
8
H
H
9
-(CH2)5-
-(CH2)5-
10
11
12
13
14
15
16
H
2j
CH3
CH3
H
CH3
CH3
H
H
2k
2l
H
H
2m
2n
2o
2p
H
H
C6H5
H
C6H5S
-(CH2)5-
C6H5S
CH3
CH3
H
C6H5S
a Isolated yields based on the allenyl sulfoxides.
meter. Elemental analyses were performed on an EA-1110
instrument.
O
PdCl2/CuI
O
SPh
MeOH/Et3N
SPh
PhTe
(b-Organochalcogenyl)allyl Phenyl Sulfoxides 2a–p; General
Procedure
H
2d
3 Yield = 58%
MeO
OMe
A solution of allenyl sulfoxide 1 (0.5 mmol) in EtOH (2 mL) was
added dropwise to a solution of RYNa, prepared in situ by reduction
of (R4Y)2 (0.25 mmol) with NaBH4 (0.6 mmol) in EtOH (2 mL) at
r.t. under N2. After completion of the reaction (5 min), the mixture
was diluted with brine (10 mL) and extracted with EtOAc (3 × 15
mL). The combined organic layers were dried (MgSO4) and filtered.
Removal of the solvent in vacuo, and purification of the residue by
silica gel chromatography with n-hexane–EtOAc (5:1) as eluent
gave the product 2.
Scheme 2
O
SO2Ph
MCPBA
CH2Cl2
SPh
PhO2S
PhS
4
2m
Yield = 85%
Scheme 3
2a
Yellow oil.
In summary, we have disclosed here the high efficient re-
gioselective hydrohalcogenation of allenyl sulfoxides to
afford synthetically important (b-organochalcogenyl)allyl
phenyl sulfoxides. The application of (b-phenyltelluro)al-
lyl phenyl sulfoxide 2d and (b-organosulfanyl)allyl phe-
nyl sulfoxide 2m in organic synthesis has also been
described.
IR (neat): 1610, 1040 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.86–7.82 (m, 2 H), 7.54–7.48 (m,
6 H), 7.37–7.24 (m, 2 H), 6.06 (s, 1 H), 5.71 (s, 1 H), 3.82 (d,
J = 13.2 Hz, 1 H), 3.49 (d, J = 8.8 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 142.9, 139.9, 131.6, 131.2, 129.7,
129.4, 129.0, 124.3, 115.1, 113.2, 69.6.
MS (EI): m/z = 373 [M+ + 1].
All 1H and 13C NMR spectra were measured in CDCl3 and recorded
on Bruker Avance-400 (400 MHz) spectrometer with TMS as the
internal standard. Chemical shifts are expressed in ppm and J values
are given in Hz. IR spectra were run on a Bruker vector 22 spec-
trometer. EIMS were determined with a HP5989B mass spectro-
Anal. Calcd for C15H14OSTe: C, 48.70; H, 3.81. Found: C, 48.64; H,
3.93.
2b
Yellow oil.
Synthesis 2005, No. 13, 2171–2175 © Thieme Stuttgart · New York

PAPER
Synthesis of (b-Organochalcogenyl)allyl Phenyl Sulfoxides
2173
IR (neat): 1625, 1040 cm–1.
2g
Oil.
1H NMR (400 MHz, CDCl3): d = 7.82–7.80 (m, 2 H), 7.39–7.31 (m,
10 H), 7.28–7.20 (m, 3 H), 4.2 (s, 2 H), 2.1 (s, 1 H).
IR (neat): 1637, 1032 cm–1.
13C NMR (100 MHz, CDCl3): d = 143.2, 141.8, 140.0, 138.7, 135.2,
129.4, 128.5, 128.4, 128.2, 127.7, 124.1, 111.4, 70.0.
1H NMR (400 MHz, CDCl3): d = 7.48–7.46 (m, 3 H), 7.41–7.35 (m,
3 H), 7.34–7.29 (m, 4 H), 7.25–7.21 (m, 5 H), 4.19 (s, 2 H), 1.77 (s,
1 H).
MS (EI): m/z = 449 [M+ + 1].
13C NMR (100 MHz, CDCl3): d = 145.3, 141.5, 140.2, 138.4, 135.0,
129.1, 128.5, 127.9, 127.4, 127.0, 124.1, 112.4, 69.5.
Anal. Calcd for C21H18OSTe: C, 56.55; H, 4.07. Found: C, 56.63; H,
3.98.
MS (EI): m/z = 399 [M+ + 1].
2c
Yellow oil.
Anal. Calcd for C21H18OSSe: C, 63.47; H, 4.57. Found: C, 63.35; H,
4.64.
IR (neat): 1620, 1034 cm–1.
2h
Oil.
1H NMR (400 MHz, CDCl3): d = 7.72–7.70 (m, 2 H), 7.43–7.40 (m,
5 H), 7.30–7.29 (m, 1 H), 7.24–7.20 (m, 2 H), 4.25 (d, J = 12.8 Hz,
1 H), 3.79 (d, J = 13.2 Hz, 1 H), 2.44–240 (m, 2 H), 2.39–2.36 (m,
1 H), 2.15–2.10 (m, 1 H), 1.51–1.49 (m, 5 H), 1.46–1.33 (m, 1 H).
IR (neat): 1645, 1038 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.51–7.49 (m, 2 H), 7.38 (m, 5 H),
7.26–7.20 (m, 3 H), 4.37 (s, 2 H), 2.75 (t, J = 7.2 Hz, 2 H), 2.04 (s,
1 H), 1.60 (m, 2 H), 1.32 (m, 2 H), 0.83 (t, J = 7.2 Hz, 3 H).
13C NMR (100 MHz, CDCl3): d = 156.4, 143.5, 138.7, 130.9, 129.5,
128.9, 128.1, 124.4, 114.3, 98.8, 66.0, 41.6, 31.5, 28.1, 28.0, 26.2.
MS (EI): m/z = 441 [M+ + 1].
13C NMR (100 MHz, CDCl3): d = 143.5, 135.2, 132.5, 130.2, 129.6,
129.0, 128.3, 126.5, 124.3, 112.6, 68.3, 30.2, 27.8, 23.6, 13.4.
Anal. Calcd for C20H22OSTe: C, 54.84; H, 5.06. Found: C, 54.76; H,
5.18.
MS (EI): m/z = 379 [M+ + 1].
Anal. Calcd for C19H22OSSe: C, 60.47; H, 5.88. Found: C, 60.38; H,
5.80.
2d
Yellow oil.
IR (neat): 1615, 1036 cm–1.
2i
Oil.
1H NMR (400 MHz, CDCl3): d = 7.75–7.73 (m, 2 H), 7.41–7.39 (m,
5 H), 7.32–7.30 (m, 1 H), 7.25–7.21 (m, 2 H), 4.26 (d, J = 13.2 Hz,
1 H), 3.71 (d, J = 13.2 Hz, 1 H), 2.0 (s, 3 H), 1.70 (s, 3 H).
IR (neat): 1630, 1034 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.52–7.51 (m, 2 H), 7.50–7.38 (m,
5 H), 7.25–7.20 (m, 3 H), 4.11 (d, J = 13.2 Hz, 1 H), 3.63 (d,
J = 12.8 Hz, 1 H), 2.63–2.60 (m, 1 H), 2.52–2.49 (m, 1 H), 2.30–
2.25 (m, 1 H), 2.06–2.03 (m, 1 H), 1.53–1.47 (m, 5 H), 1.36–1.34
(m, 1 H).
13C NMR (100 MHz, CDCl3): d = 148.2, 143.6, 138.9, 130.9, 129.6,
128.9, 128.2, 124.2, 114.0, 101.6, 66.6, 30.4, 20.9.
MS (EI): m/z = 400 [M+ + 1].
Anal. Calcd for C17H18OSTe: C, 51.30; H, 4.56. Found: C, 51.45; H,
4.48.
13C NMR (100 MHz, CDCl3): d = 154.9, 143.7, 132.1, 130.9, 130.5,
129.3, 128.9, 127.0, 124.3, 111.3, 64.2, 36.2, 31.9, 28.1, 28.0, 26.1.
2e
Oil.
MS (EI): m/z = 391 [M+ + 1].
Anal. Calcd for C20H22OSSe: C, 61.69; H, 5.69. Found: C, 61.75; H,
5.60.
IR (neat): 1628, 1040 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.55–7.53 (m, 4 H), 7.51–7.45 (m,
3 H), 7.32–7.29 (m, 3 H), 5.6 (s, 1 H), 5.42 (s, 1 H), 3.72 (d, J = 13.2
Hz, 1 H), 3.51 (d, J = 12.8 Hz, 1 H).
2j
Oil.
IR (neat): 1628, 1035 cm–1.
13C NMR (100 MHz, CDCl3): d = 143.3, 135.0, 131.2, 130.6, 129.5,
129.0, 128.5, 127.7, 124.2, 123.7, 66.7.
1H NMR (400 MHz, CDCl3): d = 7.60–7.59 (m, 2 H), 7.44–7.43 (m,
3 H), 4.16 (d, J = 12.4 Hz, 1 H), 3.79 (d, J = 12.8 Hz, 1 H), 2.63 (t,
J = 7.2 Hz, 2 H), 2.56–2.53 (m, 1 H), 2.42–2.39 (m, 1 H), 2.10–2.07
(m, 1 H), 1.86–1.85 (m, 1 H), 1.58–1.52 (m, 2 H), 1.46–1.40 (m, 3
H), 1.39–1.32 (m, 4 H), 1.18–1.16 (m, 1 H), 0.85 (t, J = 7.2 Hz, 3
H).
MS (EI): m/z = 323 [M+ + 1].
Anal. Calcd for C15H14OSSe: C, 56.07; H, 4.39. Found: C, 56.14; H,
4.30.
2f
Oil.
13C NMR (100 MHz, CDCl3): d = 153.9, 144.6, 130.9, 128.9, 124.5,
109.9, 65.2, 36.0, 32.2, 31.5, 27.9, 27.8, 26.7, 26.1, 22.8, 13.5.
IR (neat): 1625, 1043 cm–1.
MS (EI): m/z = 371 [M+ + 1].
1H NMR (400 MHz, CDCl3): d = 7.53–7.52 (m, 2 H), 7.38–7.36 (m,
3 H), 5.39 (s, 1 H), 5.11 (s, 1 H), 3.67 (d, J = 12.8 Hz, 1 H), 3.44 (d,
J = 12.8 Hz, 1 H), 2.64 (t, J = 7.2 Hz, 3 H), 1.58–1.51 (m, 2 H), 1.31
(m, 2 H), 0.79 (t, J = 7.2 Hz, 3 H).
Anal. Calcd for C18H26OSSe: C, 58.52; H, 7.09. Found: C, 58.60; H,
7.15.
2k
Oil.
13C NMR (100 MHz, CDCl3): d = 143.4, 131.2, 129.6, 128.9, 124.3,
119.5, 67.9, 31.2, 26.3, 22.9, 13.5.
IR (neat): 1645, 1045 cm–1.
MS (EI): m/z = 303 [M+ + 1].
1H NMR (400 MHz, CDCl3): d = 7.52–7.50 (m, 2 H), 7.45–7.42 (m,
5 H), 7.28–7.26 (m, 3 H), 4.08 (d, J = 13.2 Hz, 1 H), 3.58 (d,
J = 13.2 Hz, 1 H), 2.06 (s, 3 H), 1.70 (s, 3 H).
Anal. Calcd for C13H18OSSe: C, 51.82; H, 6.02. Found: C, 51.91; H,
5.97.
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13C NMR (100 MHz, CDCl3): d = 146.7, 143.5, 131.0, 128.8, 124.2,
112.5, 65.4, 32.3, 26.3, 25.8, 22.9, 20.9, 13.6.
IR (neat): 1618, 1050 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.54–7.46 (m, 5 H), 7.29–7.17 (m,
5 H), 4.01 (d, J = 12.0 Hz, 1 H), 3.52 (d, J = 12.0 Hz, 1 H), 2.06 (s,
3 H), 1.78 (s, 1 H).
MS (EI): m/z = 351 [M+ + 1].
Anal. Calcd for C17H18OSSe: C, 58.45; H, 5.19. Found: C, 58.39; H,
5.25.
13C NMR (100 MHz, CDCl3): d = 148.7, 134.9, 131.0, 131.1, 129.1,
129.0, 128.9, 126.4, 124.2, 116.2, 65.2, 23.7, 21.8.
2l
Oil.
MS (EI): m/z = 303 [M+ + 1].
Anal. Calcd for C17H18OS2: C, 67.51; H, 6.00. Found: C, 67.60; H,
5.89.
IR (neat): 1640, 1048 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.68–7.66 (m, 2 H), 7.53–7.51 (m,
2 H), 4.19 (d, J = 12.4 Hz, 1 H), 3.81 (d, J = 12.8 Hz, 1 H), 2.74 (t,
J = 7.2 Hz, 2 H), 2.0 (s, 3 H), 1.67–1.61 (m, 2 H), 1.53 (s, 3 H),
1.47–1.41 (m, 2 H), 0.94 (t, J = 7.2 Hz, 3 H).
5-Methoxy-2-(1-methylethylidene)pent-3-ynyl Phenyl Sulfox-
ide (3)
A mixture of 2d (398 mg, 1 mmol), 3-methoxypropyne (140 mg, 2.0
mmol), PdCl2 (10 mol%), CuI (10 mol%) and Et3N (101 mg, 1.0
mmol) in MeOH (2 mL) was stirred at r.t. for 24 h under N2. After
completion of the reaction, the mixture was diluted with brine (10
mL) and extracted with EtOAc (3 × 15 mL). The organic layer was
dried (MgSO4). After filtration and removal of the solvent in vacuo,
the residue was purified via chromatography on silica gel with n-
hexane–EtOAc (3:1) as the eluent to give 3 as an oil; yield: 152 mg
(58%).
13C NMR (100 MHz, CDCl3): d = 145.7, 143.5, 131.0, 128.8, 124.2,
112.5, 65.4, 32.3, 26.3, 25.8, 22.9, 20.9, 13.6.
MS (EI): m/z = 331 [M+ + 1].
Anal. Calcd for C15H22OSSe: C, 54.70; H, 6.73. Found: C, 54.81; H,
6.62.
2m
Oil.
IR (KBr): 2230, 1605, 1049 cm–1.
IR (neat): 1618, 1050 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.65–7.64 (m, 2 H), 7.50–7.48 (m,
3 H), 4.19 (s, 2 H), 3.89 (d, J = 12.0 Hz, 1 H), 3.55 (d, J = 12.4 Hz,
1 H), 3.38 (s, 3 H), 1.96 (s, 3 H), 1.50 (s, 3 H).
1H NMR (400 MHz, CDCl3): d = 7.67 (m, 5 H), 7.42–7.40 (m, 2 H),
7.37–7.28 (m, 3 H), 5.27 (s, 1 H), 5.18 (s, 1 H), 3.70 (d, J = 12.4 Hz,
1 H), 3.46 (d, J = 12.4 Hz, 1 H).
13C NMR (100 MHz, CDCl3): d = 149.4, 143.2, 131.2, 128.8, 124.4,
106.3, 88.3, 85.4, 61.4, 60.2, 57.5, 24.0, 20.2.
13C NMR (100 MHz, CDCl3): d = 143.5, 134.6, 133.5, 131.4, 129.4,
129.2, 129.0, 128.5, 124.2, 11.9, 63.7.
MS (EI): m/z = 263 [M+ + 1].
MS (EI): m/z = 275 [M+ + 1].
Anal. Calcd for C15H18O2S: C, 68.67; H, 6.92. Found: C, 68.76; H,
6.81.
Anal. Calcd for C15H14OS2: C, 65.66; H, 5.14. Found: C, 65.54; H,
5.21.
2,3-Bis(phenylsulfonyl)prop-1-ene (4)
To a solution of 2m (274 mg, 1 mmol) in CH2Cl2 (5 mL) was added
MCPBA (690 mg, 5 mmol) at 0 °C, then the temperature was al-
lowed to warm up to r.t. After completion of the reaction (TLC), the
mixture was quenched with aq NH4Cl (5 mL), and extracted with
Et2O (3 × 15 mL). The combined Et2O extracts were dried
(Mg2SO4) and filtered. Removal of the solvent in vacuo afforded the
crude product, which was purified by flash chromatography (hex-
ane–EtOAc, 3:1) to afford 4; yield: 274 mg (85%); mp 128–129 °C
(Lit12 mp 128–129.5 °C).
2n
Oil.
IR (neat): 1608, 1049 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.51–7.49 (m, 2 H), 7.41–7.36 (m,
3 H), 7.34–7.30 (m, 6 H), 7.29–7.24 (m, 4 H), 4.20 (s, 2 H), 1.68 (s,
1 H).
13C NMR (100 MHz, CDCl3): d = 145.2, 140.5, 140.2, 139.4, 138.4,
135.1, 128.6, 127.9, 127.4, 127.0, 124.1, 113.4, 68.9.
1H NMR (400 MHz, CDCl3): d = 7.54–7.40 (m, 2 H), 7.38–7.35 (m,
3 H), 7.32–7.24 (m, 5 H), 6.80 (s, 1 H), 5.21 (s, 1 H), 3.70 (s, 2 H).
MS (EI): m/z = 351 [M+ + 1].
Anal. Calcd for C21H18OS2: C, 71.96; H, 5.18. Found: C, 72.05; H,
5.06.
Acknowledgment
2o
Oil.
We are grateful to the National Natural Science Foundation of
China (Project No. 20272050, 20332060) for financial support.
IR (neat): 1635, 1030 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.62–7.56 (m, 2 H), 7.55–7.50 (m,
3 H), 7.29–7.25 (m, 2 H), 7.20–7.15 (m, 3 H), 4.04 (d, J = 12.8 Hz,
1 H), 3.54 (d, J = 12.8 Hz, 1 H), 2.69–2.66 (m, 1 H), 2.57–2.54 (m,
1 H), 2.32–2.27 (m, 1 H), 2.11–2.07 (m, 1 H), 1.56–1.51 (m, 5 H),
1.39 (m, 1 H).
References
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13C NMR (100 MHz, CDCl3): d = 156.7, 143.6, 135.3, 131.0, 129.1,
129.0, 128.8, 126.2, 124.3, 113.1, 62.6, 33.5, 32.1, 28.1, 28.0, 26.1.
MS (EI): m/z = 343 [M+ + 1].
Anal. Calcd for C20H22OS2: C, 70.13; H, 6.47. Found: C, 70.21; H,
6.35.
2p
Oil.
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Synthesis of (b-Organochalcogenyl)allyl Phenyl Sulfoxides
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Synthesis 2005, No. 13, 2171–2175 © Thieme Stuttgart · New York