The oxysulfenylation of alkenes with dimethyl sulfoxide/oxalyl chloride

Article abstract of DOI:10.1080/00397911.2019.1639192

A convenient method for the oxysulfenylation of alkenes using dimethyl sulfoxide/oxalyl chloride is described. Cycloalkenes give trans-adducts stereospecifically. The reactions of styrene are highly regioselective for Markovnikov adducts, whereas aliphati

Full text of DOI:10.1080/00397911.2019.1639192

Synthetic Communications
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The oxysulfenylation of alkenes with dimethyl
sulfoxide/oxalyl chloride
Yongguo Liu, Yang Gao, Zhitong Wang, Jian Dong, Rui Ding, Baoguo Sun &
Hongyu Tian
To cite this article: Yongguo Liu, Yang Gao, Zhitong Wang, Jian Dong, Rui Ding, Baoguo Sun
& Hongyu Tian (2019): The oxysulfenylation of alkenes with dimethyl sulfoxide/oxalyl chloride,
Synthetic Communications, DOI: 10.1080/00397911.2019.1639192
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https://doi.org/10.1080/00397911.2019.1639192
The oxysulfenylation of alkenes with dimethyl sulfoxide/
oxalyl chloride
Yongguo Liu, Yang Gao, Zhitong Wang, Jian Dong, Rui Ding, Baoguo Sun, and
Hongyu Tian
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key laboratory of
Flavor Chemistry, Beijing Technology and Business University, Beijing, China
ABSTRACT
ARTICLE HISTORY
Received 22 February 2019
A convenient method for the oxysulfenylation of alkenes using
dimethyl sulfoxide/oxalyl chloride is described. Cycloalkenes give
trans-adducts stereospecifically. The reactions of styrene are highly
regioselective for Markovnikov adducts, whereas aliphatic alkenes
lead to anti-Markovnikov adducts mainly.
KEYWORDS
Alkenes; dimethyl sulfoxide;
oxysulfenylation;
oxalyl chloride
GRAPHICAL ABSTRACT
Introduction
The construction of carbon–sulfur bond has been investigated actively in organic syn-
thesis since sulfur-containing compounds can be used in many different fields, such as
pharmaceutical industry, agricultural chemicals, and material science.[1–4]
Oxysulfenylation of olefins provides a very efficient approach to introduce a C–S bond
as well as an adjacent C–O bond concurrently. Many methods for oxysulfenylation of
olefins have been developed in recent years, which generally involve the addition of an
active sulfur-containing species originated from various sulfenylating agents, such as thi-
osulfates,[5] arylsulfonyl chlorides,[6] arylsulfinic acids,[7] sulfonyl hydrazides,[8] sulfi-
nates,[9] sulfonamides,[10–12] disulfides,[13–15] or dimethyl sulfoxide,[16] to the double
bond of an alkene. It also can be achieved by electrochemical oxidative addition of
CONTACT Hongyu Tian
tianhy@btbu.edu.cn
Beijing Advanced Innovation Center for Food Nutrition and Human
Health, Beijing Key laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, China.
Supplemental data for this article is available online at on the publisher’s website.
ß 2019 Taylor & Francis Group, LLC

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Y. LIU ET AL.
Scheme 1. Oxysulfenylation of alkenes with DMSO/(COCl)2 and carboxylic acids or alcohols.
thiols and alcohols to alkenes.[17] Although there are so many choices for the oxysulfe-
nylation of alkenes, most of them suffer from more or less drawbacks, such as high
cost, harsh reaction conditions, or lack of generality. Therefore, readily available and
efficient reagents are still highly desirable.
The combined reagents of R2SO (R ¼ Me or Ph) and (COX)2 (X ¼ Cl or Br) have
been found to be very useful for some transformations, such as sulfenyllactonization[18]
or chlorolactonization[19] of alkenoic acids, preparation of a,b-unsaturated-c-lactones
from alkenoic acids,[20] bromination[21] or sulfenylchlorination[22] of alkenes, sulfenyle-
therification of unsaturated alcohols[23] in our recent work. Based on these results, it is
conceivable that the oxysulfenylation of alkenes could be achieved by using Me2SO/
(COCl)2 and oxygen-containing nucleophiles. Therefore, we investigated the reactions
of a series of alkenes with Me2SO/(COCl)2 and carboxylic acids or alcohols in this pre-
sent work (Scheme 1).
Results and discussion
Oxysulfenylation of alkenes with carboxylic acids as nucleophiles
The reactions of a series of alkenes with benzoic acid or acetic acid in the presence of
DMSO/(COCl)2 were investigated under the conditions similar to those for sulfenyllac-
tonization in our previous work (entries 1–8, Table 1).[18] First, 1.5 equiv. of (COCl)2
were added to 3 equiv. of DMSO in CH3CN at ꢀ5 ꢁC to generate the key sulfenylating
agent CH3SCl, then 1 equivalent of an alkene, 1.2 equiv. of PhCOOH or CH3COOH, 5
equiv. of K2CO3 and 0.1 equiv. of 18-Crown-6 were added to the mixture. After add-
ition, the reaction mixture was warmed up and heated to reflux. The reaction completed
in 4–8 h to produce the corresponding adducts 2a–h in 75–87% yields.
Both cycloalkenes, cyclohexene 1a and cycloheptene 1b, were converted to the single
adducts 2a and 2b stereospecifically (entries 1 and 2). For the substrate cyclohexene 1a,
the product 1-benzoyloxy-2-methylthiocyclohexane 2a was determined to be trans con-
figuration based on the magnitude of the coupling constant between HC1 and HC2
(3J ¼ 8.7 Hz). For the substrate cycloheptene 1b, the relative configuration of the prod-
uct 1-benzoyloxy-2-methylthiocycloheptane 2b was determined to be trans based on the
NOE experiment, in which the intensity of the signal of methylthio group was enhanced
by 1.5% when the signal of HC1 was irradiated. This stereoselectivity should be due to

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Table 1. Oxysulfenylation of Alkenes with DMSO/(COCl)2.
Entry
Substrate
oxygen-containing
Product
Isolated
yield (%)
alkene
nucleophile
PhCOOH
1
81
75
78
1a
2a
2b
2c
2d
2
3
4
5
PhCOOH
PhCOOH
PhCOOH
PhCOOH
1b
1c
77
(4:1)a
1d
83
(5:1)a
1e
2e
6
7
8
9
PhCOOH
CH3COOH
CH3COOH
76
1f, R =
n-octyl
(2.5:1)a
2f, R = n-octyl
87
1c
2g
84
(5:1)a
1f, R =
n-octyl
2h, R = n-octyl
89
1a
3a
(continued)

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Y. LIU ET AL.
Table 1. Continued.
10
82
80
1b
3b
11
1c
3c
12
85
(1.8:1)a
1d
3d
3d´
13
84
(6:1)a
1e
3e
14
83
(1.5:1)a
1f, R =
n-octyl
3f, R = n-octyl
3f´, R = n-octyl
15
CH3OH
95
1c
3g
aThe product obtained is a mixture of anti-Markovnikov and Markovnikov adducts with a ratio shown in parentheses.
the involvement of the intermediates thiiranium ions formed by the electrophilic add-
ition of CH3SCl to the double bond of the cycloalkenes, which is consistent with that in
the sulfenyllactonization of alkenoic acids in our previous work.[18] Among the four ter-
minal alkenes, only styrene 1c gave a single Markovnikov adduct, 1-benzoyloxy-1-phe-
nyl-2-methylthioethane 2c when PhCOOH was used as a nucleophile (entry 3). In
contrast, the anti-Markovnikov adducts 2d–f were obtained as the major products for
the other three terminal alkenes 1d–f (entries 4–6). In order to explore the regioselectiv-
ity of the reaction of styrene 1c further, a reaction was carried out using CH3COOH as

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Scheme 2. The regioselectivity of terminal alkenes
a nucleophile, which also afforded a single Markovnikov adduct, 1-acetoxy-1-phenyl-2-
methylthioethane 2g (entry 7). In comparison, the reaction of 1-decene 1f with
CH3COOH still generated the anti-Markovnikov adduct 1-acetoxy-2-methylthiodecane
2h as the major product (entry 8). The high regioselectivity of the reactions of styrene
1c for Markovnikov adducts can be interpreted as more carboniumion character of the
intermediate thiiranium ion is brought about by phenyl group attached directly to the
thiiranium ring. For the other three terminal alkenes 1d–f, the reactions are kinetically
controlled to produce anti-Markovnikov adducts (Scheme 2). Muangkaew et al. also
reported this regioselectivity for anti-Markovnikov adducts in PhI(OAc)2/KI mediated
1,2-acetoxysulfenylation of aliphatic alkenes.[13] However, it is interesting to note that
these terminal alkenes produced the corresponding Markovnikov adducts as major
products in the sulfenylchlorination with Me2SO/(COCl)2 we reported before.[22]
Obviously, chloride ion and carboxylate ions show different preference when they attack
the intermediates thiiranium ions in these reactions, which might be related to steric
effects of these nucleophiles.
It is also noteworthy that the sulfenyllactonization of alkenoic acids were able to be
done without the aid of K2CO3 in our previous work.[18] However, the addition of
K2CO3 is necessary for the production of the adducts in our present work, which may
be due to the difference between the intramolecular and intermolecular reactions. The
adducts were generated by an intermolecular nucleophilic attack of PhCOOH or
CH3COOH on the intermediates thiiranium ions in this present work, which might be
more difficult to occur than the intramolecular attack in the sulfenyllactonization of
alkenoic acids.[18]
Oxysulfenylation of alkenes with alcohols as nucleophiles
The reactions of these alkenes with p-methylphenol in the presence of DMSO/(COCl)2
were also explored under the conditions the same as above. The corresponding adducts
3a–f were obtained in 83–89% yields (entries 9–14, Table 1). Likewise, the two cycloal-
kenes, cyclohexene 1a and cycloheptene 1b produced the trans adducts 3a and 3b
stereospecifically (entries 9 and 10), which was determined by the coupling constant

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Y. LIU ET AL.
3
between HC1 and HC2 (3a, J ¼ 8.4 Hz) or the NOE experiment (3b), in which the
intensity of the signal of methylthio group was enhanced by 1.0% when the signal of
HC1 was irradiated. Among the four terminal alkenes, styrene 1c still is the only one
substrate to give a single Markovnikov adduct, 1-p-methylphenyloxy-1-phenyl-2-methyl-
thioethane 3c (entry 11), whereas the other three terminal alkenes 1d–f produced the
anti-Markovnikov adducts 3d–f as the major products (entries 12–14). For styrene 1c,
one more reaction was carried out using CH3OH as a nucleophile to examine the regio-
selectivity, which gave a single Markovnikov adduct, 1-methoxy-1-phenyl-2-methylthio-
ethane 3h as expected (entry 15). The regioselectivity of the reactions of 1c with
alcohols is consistent with that of the above reactions with carboxylic acids. The reac-
tions of the substrates 1d and 1f with p-methylphenol (entries 12 and 14) show much
poorer regioselectivity than the reaction of cyclohexylethene 1e (entry 13). These results
should be due to the steric hindrance effect of relatively bulky cyclohexyl group attached
to the double bond of 1e, which favors the formation of the kinetically controlled prod-
uct. Compared with the reactions of 1d and 1f with benzoic acids (entries 4 and 6), the
regioselectivity of the reactions with p-methylphenol was observed to decrease to some
extent (entries 12 and 14).
Conclusion
In summary, we demonstrate a convenient approach of oxysulfenylation of alkenes
by using the combination of DMSO and oxalyl chloride, which can introduce vari-
ous acetoxy or alkoxy groups as well as methylthio group on two adjacent carbons.
The method has several prominent advantages, such as readily available reagents,
mild reaction conditions, and good yields, which affords another reliable alternative
for the preparation of functionalized sulfur-containing compounds.
Experimental
1H NMR spectra were recorded on a Bruker AV300 or 600 spectrometer. 13C NMR
spectra were recorded at 75 or 150 MHz. Chemical shifts were reported in parts per mil-
lion (ppm). The residual solvent peak was used as an internal reference. HRMS data
were obtained on a Solarix Mass Spectrometer. Analytical thin layer chromatography
(TLC) was performed with precoated TLC plates, silica gel 60 F-254, layer thickness
0.25 mm. Flash chromatography separations were performed on 230–400 mesh silica
gel. Reagents and solvents are commercial grade and were used as supplied. The relative
spectra and data of all the products are available in the Supporting Information Section.
General procedure for the oxysulfenylation of alkenes
To a solution of dimethylsulfoxide (DMSO 1.3 mL, 15 mmol, 3.0 equiv.) in acetonitrile
(15 mL) cooled at ꢀ5 ꢁC was added dropwise a solution of oxalyl chloride (0.7 mL,
7.5 mmol, 1.5 equiv.) in acetonitrile (10 mL). After 10 min, a solution of an alkene
(5 mmol, 1.0 equiv.) and PhCOOH or p-methylphenol (6 mmol, 1.2 equiv.) in aceto-
nitrile (20 mL), K2CO3 (5 equiv.) and 18-Crown-6 (0.1 equiv.) were added successively.

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The reaction mixture was then allowed to warm to room temperature and heated to
reflux. The reaction progress was monitored using TLC. After completion of the reac-
tion, acetonitrile was removed and a saturated aqueous solution of NH4Cl (30 mL) was
added. The mixture was extracted with CH2Cl2 (3 ꢂ 25 mL), and the combined organic
layers were dried over MgSO4. After evaporation of the solvent, the residue was purified
using chromatography (20:1, petroleum ether/EtOAc) to give the product.
Trans-1-benzoyloxy-2-methylthiocyclohexane (2a)
1
Light yellow oil (1.01 g, 81%). HNMR (300 MHz, CDCl3): d 7.97 (m, 2 H, HC20 and 60
(phenyl)), 7.44 (m, 1 H, HC40 (phenyl)), 7.33 (m, 2 H, HC30 and 50 (phenyl)), 4.95 (td,
J ¼ 8.7, 3.9 Hz, 1 H, HC1), 2.67 (ddd, J ¼ 9.9, 8.7, 4.2 Hz, 1 H, HC2), 1.98-2.14 (m, 2 H,
HC3 and 6), 2.02 (s, 3 H, SCH3), 1.57-1.74 (m, 2 H, HC4 and 5), 1.26-1.56 (m, 4 H,
13
H0C3-6). C NMR (75 MHz, CDCl3): d 165.7 (C ¼ O), 132.8 (C40 (phenyl)), 130.6 (C10
(phenyl)), 129.6 (C20 and 60 (phenyl)), 128.3 (C30 and 50 (phenyl)), 74.9 (C1), 48.3 (C2),
30.9 (C6), 30.8 (C3), 24.8 (C4), 23.5 (C5), 14.3 (SCH3). HRMS (ESI): calcd for
C14H18NaO2S [M þ Na]þ 273.0919, found 273.0920.
1-Benzoyloxy-1-phenyl-2-methylthioethane (2c)
1
Light yellow oil (1.06 g, 78%). HNMR (300 MHz, CDCl3): d 8.11 (m, 2 H, HC200 and 600
(benzoyloxy)), 7.57 (m, 1 H, HC400 (benzoyloxy)), 7.30–7.52 (m, 7 H, HC300 and 500 (ben-
zoyloxy) and HC20-60 (phenyl)), 6.17 (dd, J ¼ 7.8, 6.0 Hz, 1 H, HC1), 3.16 (dd, J ¼ 13.8,
7.5 Hz, 1 H, HC2), 3.00 (dd, J ¼ 13.8, 5.7 Hz, 1 H, H0C2), 2.13 (s, 3 H, SCH3). 13C NMR
(75 MHz, CDCl3): d 165.6 (C ¼ O), 139.4 (C10 (phenyl)), 133.1 (C400 (benzoyloxy)),
130.2 (C100 (benzoyloxy)), 129.7 (C200 and 600 (benzoyloxy)), 128.6 (C300 and 500 (benzoy-
loxy)), 128.43 (C30 and 50 (phenyl)), 128.41 (C40 (phenyl)), 126.6 (C20 and 60 (phenyl)),
75.3 (C1), 40.4 (C2), 16.4 (SCH3). HRMS (ESI): calcd for C16H16NaO2S [M þ Na]þ
295.0763, found 295.0763.
Trans-1-p-methylphenyloxy-2-methylthiocyclohexane (3a)
1
Light yellow oil (1.05 g, 89%). HNMR (300 MHz, CDCl3): d 7.07 (d, J ¼ 8.4 Hz, 2 H,
HC30 and 50 (phenyl)), 6.85 (d, J ¼ 8.4 Hz, 2 H, HC20 and 60 (phenyl)), 4.12 (td, J ¼ 8.4,
3.9 Hz, 1 H, HC1), 2.81 (ddd, J ¼ 9.6, 8.4, 3.9 Hz, 1 H, HC2), 2.28 (s, 3 H, CH3 (phenyl))
2.20 (s, 3 H, SCH3), 2.06–2.20 (m, 2 H, HC3 and 6), 1.67–1.81 (m, 2 H, HC4 and 5),
13
1.23–1.55 (m, 4 H, H0C3-6). C NMR (75 MHz, CDCl3): d 155.6 (C10 (phenyl)), 130.3
(C40 (phenyl)), 129.9 (C30 and 50 (phenyl)), 116.4 (C20 and 60 (phenyl)), 80.8 (C1), 49.5
(C2), 30.7 (C3), 30.5 (C6), 24.7 (C4), 23.2 (C5), 20.5 (CH3 (phenyl)), 14.3 (SCH3).
HRMS (ESI): calcd for C14H20NaOS [M þ Na]þ 259.1127, found 259.1127.
1-p-Methylphenyloxy-1-phenyl-2-methylthioethane (3c)
1
Light yellow oil (1.03 g, 80%). HNMR (600 MHz, CDCl3): d 7.41 (d, J ¼ 7.8 Hz, 2 H,
HC20 and 60 (phenyl)), 7.35 (t, J ¼ 7.8 Hz, 2 H, HC30 and 50 (phenyl)), 7.28 (t, J ¼ 7.8 Hz,

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Y. LIU ET AL.
1 H, HC40 (phenyl)), 6.99 (d, J ¼ 8.4 Hz, 2 H, HC300 and 500 (p-methylphenyl)), 6.77 (d,
J ¼ 8.4 Hz, 2 H, HC200 and 600 (p-methylphenyl)), 5.24 (dd, J ¼ 7.8, 4.8 Hz, 1 H, HC1),
3.11 (dd, J ¼ 13.8, 7.8 Hz, 1 H, HC2), 2.88 (dd, J ¼ 13.8, 4.8 Hz, 1 H, H0C2), 2.24 (s, 3 H,
13
CH3 (phenyl)), 2.14 (s, 3 H, SCH3). C NMR (75 MHz, CDCl3): d 155.8 (C100 (p-meth-
ylphenyl)), 140.8 (C10 (phenyl)), 130.4 (C400 (p-methylphenyl)), 129.9 (C300 and 500 (p-
methylphenyl)), 128.7 (C30 and 50 (phenyl)), 128.1 (C40 (phenyl)), 126.3 (C20 and 60
(phenyl)), 116.1 (C200 and 600 (p-methylphenyl)), 81.0 (C1), 42.2 (C2), 20.5 (CH3 (phe-
nyl)), 16.9 (SCH3). HRMS (ESI): calcd for C16H18NaOS [M þ Na]þ 281.0970,
found 281.0970.
Funding
Financial support from the National Key Research and Development Program
[2016YFD0400801] and Beijing Postdoctoral Research Foundation [2017-22-011].
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