Base-Promoted Synthesis of O -Aryl/Alkyl N, N -Dimethylthiocarbamates Starting from Inexpensive and Environmentally Benign Disulfide

Article abstract of DOI:10.1055/s-0036-1588545

A series of O -aryl (alkyl) N, N -dimethylthiocarbamates were synthesized in good yields (70-77%) by reacting substituted phenols or alkyl alcohol with inexpensive, stable, and environmentally benign tetramethylthiuram disulfide (TMTD) in the presence of NaH. By avoiding use of the toxic and corrosive N, N -dialkylthiocarbamoyl chloride, the method provides a green and facile preparation for some important precursors of potentially biologically reactive compounds.

Full text of DOI:10.1055/s-0036-1588545

SYNTHESIS
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© Georg Thieme Verlag Stuttgart · New York
2017, 49, A–E
paper
A
en
Z.-B. Dong et al.
Paper
Synthesis
Base-Promoted Synthesis of O-Aryl/Alkyl N,N-Dimethylthiocarba-
mates Starting from Inexpensive and Environmentally Benign
Disulfide
Zhi-Bing Dong*a,b
Ming Wanga
Hui Zhua
Xing Liua
S
NaH
N
S
O
N
+
S
N
R
OH
R
DMF, 80 °C, 12 h
S
S
R = aryl, alkyl
70–77%, 13 examples
inexpensive and environmentally benign
Cai-Zhu Changa
a School of Chemistry and Environmental Engineering,
Wuhan Institute of Technology, Wuhan 430205, P. R.
of China
b Key Laboratory of Green Chemical Process, Ministry of
Education, Wuhan Institute of Technology, Wuhan
430205, P. R. of China
dzb04982@wit.edu.cn
Received: 29.06.2017
Accepted after revision: 19.07.2017
Published online: 22.08.2017
The synthesis of O-aryl N,N-dimethylthiocarbamates is
commonly performed with N,N-dimethylthiocarbamyl
chloride, which is toxic and corrosive.12–15 For example,
Villemin reported that phenols could be readily converted
into the corresponding O-aryldimethyl thiocarbamates by
treatment with dimethylthiocarbamyl chloride in the pres-
ence of KF/Al2O3 in MeCN (Scheme 3).14 All of these meth-
ods used toxic and corrosive reagents, which are not envi-
ronmentally sound. On the other hand, N,N-dimethylthio-
carbamyl chloride can been prepared by treating
tetramethylthiuram disulfide (TMTD) with chlorine,16 thi-
onyl chloride17,18 or phosgene–dichloromethane mixture
(Scheme 3).19 As part of our longstanding interest in ex-
panding the use of TMTD and its relevant applications,20–23
we hereby report a convenient protocol for the synthesis of
DOI: 10.1055/s-0036-1588545; Art ID: ss-2017-z0430-op
Abstract A series of O-aryl (alkyl) N,N-dimethylthiocarbamates were
synthesized in good yields (70–77%) by reacting substituted phenols or
alkyl alcohol with inexpensive, stable, and environmentally benign te-
tramethylthiuram disulfide (TMTD) in the presence of NaH. By avoiding
use of the toxic and corrosive N,N-dialkylthiocarbamoyl chloride, the
method provides a green and facile preparation for some important
precursors of potentially biologically reactive compounds.
Key words thiocarbamate, disulfide, phenols, sodium hydride, syn-
thetic methods
Thiocarbamate is an important functional group with a
wide range of application in medicines1–4 and in agrochem-
istry as pesticides.5,6 It is also a very useful intermediate in
organic synthesis.7,8 O-Aryl N,N-dimethylthiocarbamate is
an important block for a number of biologically active com-
pounds (Figure 1).9 It is also a key intermediate for the syn-
thesis of some neurokinin antagonists (Scheme 1).8 Fur-
thermore, O-aryl N,N-dimethylthiocarbamates are com-
monly used as starting material for the Newman–Kwart
rearrangement (Scheme 2).10,11
O
MeO
S
MeO
Br
O
N
N
O
NMe2
CN
S
Cl
Cl
ZD2249 methoxy sulfoxide
O-thiocarbamate
Scheme 1 O-Thiocarbamate serves as key intermediate for the synthe-
sis of ZD2249 methoxy sulfoxide (neurokinin antagonist)
X
O
Cl
N
H
O
R
R
Newman–Kwart
rearrangement
S
O
S
N
R
R
O
heat
S
X = Cl, Br, F, CF3
Scheme 2 O-Aryl N,N-dimethylthiocarbamate as starting material for
Figure 1 Compounds for potential antimicrobial drugs
the Newman–Kwart rearrangement
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–E

B
Z.-B. Dong et al.
Paper
Synthesis
Table 1 (continued)
O-aryl N,N-dimethylthiocarbamates by NaH-promoted syn-
thesis starting from inexpensive and environmentally be-
nign disulfide.
Entry Base
(equiv)
Cat. (10
%mmol)
1a/2a
Solvent
(2 mL)
Temp. Yield
(°C)
(%)a
8
9
t-BuOK (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (1.0)
NaH (0.9)
NaH (1.1)
NaH (1.2)
NaH (1.5)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
NaH (1.2)
–
1:1
DMSO
DMSO
DMF
DMAC
DMSO
PhCH3
PhNO2
THF
100
45
65
66
65
65
58
55
35
66
68
60
52
60
71
73
72
35
75
75
74
75
75
73
74
73
75
69
73
75
74
74
75
73
74
previous work
–
1:1
100
100
100
100
100
100
100
120
80
O
N
OH
Al2O3-KF, or DABCO
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
–
1:1
Cl
N
+
S
–
1:1
CH3CN, 50–65 °C
16 h
S
–
1:1
toxic and corrosive
–
1:1
Cl2 or SOCl2
–
1:1
–
1:1
this work
OH
S
–
1:1
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMF
O
N
NaH
N
S
S
–
1:1
+
N
S
DMF, 80 °C
12 h
S
–
1:1
70
inexpensive and environmentally benign
–
1:1
60
Scheme 3 Synthetic route to O-aryl N,N-dimethylthiocarbamate via
N,N-dimethylthiocarbamyl chloride or TMTD
–
1:1
80
–
1:1
80
–
1:1
80
–
1:1
80
Our investigation started by treating phenol (1a) with
TMTD 2a in the presence of a base (Table 1). Various bases
were used and it was found that sodium hydride was supe-
rior to all others (entries 1–9). Solvent screening showed
that the high boiling point solvents were better, and N,N-di-
methylformamide (DMF) was selected for the model reac-
tion (entries 9–15). Temperature screening showed that
80 °C was the optimal reaction temperature (entries 10,
16–19). Increasing the base loading to 1.2 equiv improved
the yield to 73% (entries 17, 20–23). The molar ratio of 1a to
2a of 1:1.1 gave the best reaction yield (75%; entries 22, 24–
26). The addition of metal catalysts did not have a positive
effect on the reaction (entries 27–41). The best reaction
conditions are thus summarized in entry 25.
–
1:0.5
1:1.1
1:1.3
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
1:1.2
80
–
80
80
–
CuBr
Cu2Br
CuI
80
80
80
CuCl2
Cu2O
CuO
Cu(OAc)2
CuSO4
FeCl2
FeCl3
Fe(OAc)2
NiCl2
NiBr2
Pd(OAc)2
PdCl2
80
80
80
80
80
80
Table 1 Screening Reaction Conditions for the Synthesis of O-Phenyl
N,N-Dimethylthiocarbamate Starting from TMTD and Phenol
80
80
80
S
OH
O
N
conditions
N
S
80
+
S
N
S
80
S
2a
3a
1a
80
a Isolated yield after reacting for 12 h.
Entry Base
(equiv)
Cat. (10
%mmol)
1a/2a
Solvent
(2 mL)
Temp. Yield
(°C)
(%)a
1
2
3
4
5
6
7
Na2CO3 (1.0)
K2CO3 (1.0)
Cs2CO3 (1.0)
NaOH (1.0)
KOH (1.0)
–
–
–
–
–
–
–
1:1
1:1
1:1
1:1
1:1
1:1
1:1
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
100
N.R.
By using the optimized reaction conditions, we further
investigated the substrate scope of the reaction with re-
spect to phenols, the results are summarized in Table 2.
Various substituted phenols 1a–l reacted with TMTD to
give the corresponding products with good yields (70–77%).
The results demonstrated that the standard conditions
were consistent with a number of functional groups includ-
ing fluoro, chloro, bromo, iodo, trifluoromethyl, methoxyl
100
100
100
100
100
100
N.R.
N.R.
N.R.
N.R.
40
CH3ONa (1.0)
C2H5ONa (1.0)
42
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–E

C
Z.-B. Dong et al.
Paper
Synthesis
Table 2 (continued)
and methyl groups on the aryl moiety of phenol derivatives.
It was found that the electronic nature of the phenols had
either little or no effect on the reaction, which confirmed
the versatility of this protocol. We were delighted to ob-
serve that the optimized reaction conditions could be
equally applicable to an aliphatic alcohol (1m), giving the
target molecular 3m with 70% yield.
Entry
Phenol/alcohol
Product
Yield (%)a
OH
O
S
N
9
73
F
F
1i
3i
O
S
OH
Table 2 Substrate Survey for the Synthesis of O-Aryl (alkyl) N,N-Di-
methylthiocarbamates
10
11
74
75
N
Cl
Cl
1j
3j
S
NaH
(1.2 equiv)
OH
O
N
N
S
OH
OH
O
S
+
S
N
S
DMF, 80 °C
12 h
S
N
FG
FG
2a
3
1
OCH3
OCH3
1k
1l
3k
3l
Entry
1
Phenol/alcohol
Product
Yield (%)a
75
O
S
O
S
OH
N
12
72
70
N
O
CF3
CF3
1a
3a
3b
OH
S
2
3
4
77
76
74
O
N
N
S
13b
OH
1b
1c
S
1m
3m
a Isolated yield after reacting for 12 h.
OH
O
b An example of the reaction with an aliphatic alcohol.
N
3c
Although the reaction mechanism is not clear at this
stage, we assumed that the phenol was deprotonated by
NaH, giving a reactive phenolate anion. This phenolate an-
ion then attacked the carbon atom of the thiocarbamate
through an addition–elimination reaction to furnish the fi-
nal product. Further details and relevant studies on this re-
action are under study in our laboratory.
In conclusion, a series of O-aryl N,N-dimethylthiocarba-
mates were prepared by using substituted phenols and
TMTD in the presence of NaH. Furthermore, the protocol
could be equally applied to aliphatic alcohols. The compati-
bility of a broad range of substrates, inexpensive and envi-
ronmentally benign starting materials, mild reaction condi-
tions, and good yields make this approach practical and at-
tractive for the preparation of biologically or
pharmaceutically active compounds.
OH
O
S
N
Br
Br
1d
3d
OH
O
S
N
O
5
6
7
73
76
75
Br
Br
1e
3e
OH
S
N
S
I
I
1f
3f
O
OH
N
I
I
1g
1h
3g
3h
All reactions were carried out in dried glassware fitted with septums.
All starting materials were purchased from commercial suppliers and
used without further purification, unless otherwise stated. DMSO
was dried with molecular sieves. Yields refer to isolated compounds
estimated to be >95% pure as determined by 1H NMR and capillary GC
analysis.
OH
I
O
I
N
8
74
S
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D
Z.-B. Dong et al.
Paper
Synthesis
Preparation of O-Aryl N,N-Dimethylthiocarbamates (3a) in the
O-4-Iodophenyl N,N-Dimethylthiocarbamate (3f)
Presence of NaH; Typical Procedure (TP)
White solid; mp 112–114 °C.
Phenol (1a; 1 mmol, 0.094 g) and tetramethylthiuram disulfide 2a
(TMTD, 1.1 mmol, 0.264 g) were placed in a dried glass reaction tube
equipped with a rubber stopper and then dissolved in anhydrous
DMF (2 mL). NaH (67% oil dispersion, 0.043 g, 1.2 mmol) was added
and the mixture was stirred and heated at 80 °C for 12 h. The reaction
was monitored by TLC until the starting material was consumed. The
reaction was quenched with sat. NH4Cl solution, and the mixture was
extracted with EtOAc (3 × 10 mL). The crude solution was dried over
anhydrous Na2SO4 and evaporated under vacuum. The residue was
purified by flash column chromatography (EtOAc/petroleum ether,
1:20) to afford the desired product 3a as a colorless oil (0.136 g, 75%
yield).
1H NMR (CDCl3, 400 MHz): δ = 7.76–7.59 (m, 2 H), 6.93–6.74 (m, 2 H),
3.43 (s, 3 H), 3.31 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 186.9, 153.6, 138.0, 124.9, 90.1, 43.2,
38.7.
HRMS (EI): m/z calcd. for C9H10INOS: 306.9528; found: 306.9548.
O-3-Iodophenyl N,N-Dimethylthiocarbamate (3g)
White solid; mp 110–112 °C.
1H NMR (CDCl3, 400 MHz): δ = 7.58 (d, J = 7.4 Hz, 1 H), 7.43 (s, 1 H),
7.15–7.03 (m, 2 H), 3.44 (s, 3 H), 3.32 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 187.0, 154.0, 134.9, 131.8, 130.3,
122.4, 93.1, 43.3, 38.7.
O-Phenyl N,N-Dimethylthiocarbamate (3a)
HRMS (EI): m/z calcd. for C9H10INOS: 306.9528; found: 306.9557.
Colorless oil.
1H NMR (CDCl3, 400 MHz): δ = 7.39 (t, J = 7.8 Hz, 2 H), 7.25 (t, J =
7.4 Hz, 1 H), 7.06 (d, J = 7.6 Hz, 2 H), 3.45 (s, 3 H), 3.34 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 187.7, 153.9, 129.1, 125.8, 122.7, 43.2,
O-2-Iodophenyl N,N-Dimethylthiocarbamate (3h)
White solid; mp 92–94 °C.
1H NMR (400 MHz, CDCl3): δ = 7.75 (d, J = 8.0 Hz, 1 H), 7.31 (t, J =
7.8 Hz, 1 H), 7.19 (s, 1 H), 7.06 (d, J = 8.0 Hz, 1 H), 6.92 (t, J = 8.0 Hz,
1 H), 3.41 (s, 3 H), 3.35 (s, 3 H).
38.7.
HRMS (EI): m/z calcd. for C9H11NOS: 181.0561; found: 181.0553.
13C NMR (CDCl3, 100 MHz): δ = 186.1, 154.0, 139.2, 129.1, 127.5,
124.6, 91.8, 43.5, 39.1.
O-p-Tolyl N,N-Dimethylthiocarbamate (3b)
White solid; mp 90–92 °C.
1H NMR (CDCl3, 400 MHz): δ = 7.20 (t, J = 16.0 Hz, 2 H), 6.94 (d, J =
HRMS (EI): m/z calcd. for C9H10INOS: 306.9528; found: 306.9511.
8.4 Hz, 2 H), 3.43 (s, 3 H), 3.31 (s, 3 H), 2.35 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 188.0, 151.8, 135.4, 129.7, 122.3, 43.2,
38.6, 20.9.
O-3-Fluorophenyl N,N-Dimethylthiocarbamate (3i)
Pale-yellow oil.
1H NMR (CDCl3, 400 MHz): δ = 7.34 (dd, J = 15.2, 7.6 Hz, 1 H), 6.96 (t,
J = 8.4 Hz, 1 H), 6.85 (dd, J = 18.6, 8.6 Hz, 2 H), 3.44 (s, 3 H), 3.33 (s,
3 H).
HRMS (EI): m/z calcd. for C10H13NOS: 195.0718; found: 195.0716.
O-m-Tolyl N,N-Dimethylthiocarbamate (3c)
13C NMR (100 MHz, CDCl3): δ = 187.0, 162.6 (d, 1JC–F = 247.5 Hz), 154.6
Pale-yellow oil.
3
3
4
(d, JC–F = 11.1 Hz), 129.73 (d, JC–F = 9.4 Hz), 118.7 (d, JC–F = 3.3 Hz),
1H NMR (CDCl3, 400 MHz): δ = 7.27 (dd, J = 11.2, 4.8 Hz, 1 H), 7.08–
7.02 (m, 1 H), 6.87 (d, J = 7.0 Hz, 2 H), 3.43 (s, 3 H), 3.31 (s, 3 H), 2.36
(s, 3 H).
112.9 (d, 2JC–F = 21.0 Hz), 110.9 (d, 2JC–F = 24.0 Hz), 43.2, 38.7.
HRMS (EI): m/z calcd. for C9H10FNOS: 199.0467; found: 199.0481.
13C NMR (CDCl3, 100 MHz): δ = 187.7, 153.9, 139.2, 128.7, 126.6,
123.2, 119.6, 43.1, 38.6, 21.3.
O-4-Chlorophenyl N,N-Dimethylthiocarbamate (3j)
White solid; mp 58–59 °C.
1H NMR (CDCl3, 400 MHz): δ = 7.39–7.29 (m, 2 H), 7.06–6.95 (m, 2 H),
HRMS (EI): m/z calcd. for C10H13NOS: 195.0718; found: 195.0720.
3.43 (s, 3 H), 3.32 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 187.3, 131.2, 129.1, 124.1, 43.3, 38.7.
O-4-Bromophenyl N,N-Dimethylthiocarbamate (3d)
Yellow solid; mp 84–85 °C.
1H NMR (CDCl3, 400 MHz): δ = 7.48 (d, J = 8.8 Hz, 2 H), 6.94 (d, J =
HRMS (EI): m/z calcd. for C9H10ClNOS: 215.0172; found: 215.0163.
8.8 Hz, 2 H), 3.43 (s, 3 H), 3.31 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 187.2, 152.9, 132.1, 124.5, 119.0, 43.3,
38.8.
O-3-Methoxylphenyl N,N-Dimethylthiocarbamate (3k)
Colorless oil.
1H NMR (CDCl3, 400 MHz): δ = 7.29 (t, J = 8.2 Hz, 1 H), 6.84–6.77 (m,
1 H), 6.71–6.61 (m, 2 H), 3.80 (s, 3 H), 3.45 (s, 3 H), 3.33 (s, 3 H).
HRMS (EI): m/z calcd. for C9H10BrNOS: 258.9666; found: 258.9668.
13C NMR (CDCl3, 100 MHz): δ = 187.5, 160.2, 154.8, 129.4, 114.9,
111.7, 108.7, 55.3, 43.2, 38.7.
O-3-Bromophenyl N,N-Dimethylthiocarbamate (3e)
Yellow solid; mp 83–85 °C.
1H NMR (CDCl3, 400 MHz): δ = 7.38 (d, J = 8.0 Hz, 1 H), 7.25 (dd, J = 9.2,
6.8 Hz, 2 H), 7.03 (d, J = 8.2 Hz, 1 H), 3.44 (s, 3 H), 3.32 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 187.0, 154.2, 130.0, 129.0, 126.2,
122.0, 121.81, 43.3, 38.8.
HRMS (EI): m/z calcd. for C10H13NO2S: 211.0667; found: 211.0678.
O-3-(Trifluoromethyl)phenyl N,N-Dimethylthiocarbamate (3l)
Pale-yellow oil.
1H NMR (CDCl3, 400 MHz): δ = 7.50 (d, J = 5.0 Hz, 2 H), 7.34 (s, 1 H),
7.31–7.26 (m, 1 H), 3.44 (s, 3 H), 3.34 (s, 3 H).
HRMS (EI): m/z calcd. for C9H10BrNOS: 258.9666; found: 258.9669.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–E

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Z.-B. Dong et al.
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Synthesis
2
13C NMR (CDCl3, 100 MHz): δ = 187.0, 153.9, 131.5 (q, JC–F = 32 Hz),
129.6, 126.6, 123.6 (q, 1JC–F = 270 Hz), 122.6 (q, 3JC–F = 3 Hz), 120.2 (q,
3JC–F = 3 Hz), 43.3, 38.8.
(2) Xue, M.; Long, B. H.; Fairchild, C. Bioorg. Med. Chem. Lett. 2000,
10, 1327.
(3) Harwood, J. L. Biochem. Soc. Trans. 1994, 22, 621.
(4) McElroy, N. R.; Jurs, P. C.; Morisseau, C.; Hammock, B. D. J. Med.
Chem. 2003, 46, 1066.
HRMS (EI): m/z calcd. for C10H10F3NOS: 249.0435; found: 249.0446.
(5) Lee, S. J.; Caboni, P.; Tomizawa, M.; Casida, J. E. J. Agric. Food
Chem. 2004, 52, 95.
O-2-Methylallyl N,N-Dimethylthiocarbamate (3m)
Colorless oil.
(6) Mizuno, T.; Junko, T.; Ogawa, A. Tetrahedron 2003, 59, 1327.
(7) Yuck, K. O.; Jie, E. P.; Dae, D. S. J. Org. Chem. 2004, 69, 3150.
(8) Bowden, S. A.; Burke, J. N.; Gray, F.; McKown, S.; Moseley, J. D.;
Moss, W. O.; Murray, P. M.; Welham, M. J.; Young, M. J. Org.
Process Res. Dev. 2004, 8, 33.
(9) Kratky, M.; Volkova, M.; Novotna, E.; Trejtnar, F.; Stolarikva, J.;
Vinsova, J. Bioorg. Med. Chem. 2014, 22, 4073.
(10) Burns, M.; Lloyd-Jones, G. C.; Moseley, J. D.; Renny, J. S. J. Org.
Chem. 2010, 75, 6347.
1H NMR (CDCl3, 400 MHz): δ = 5.04 (s, 1 H), 4.90 (s, 1 H), 4.01 (s, 2 H),
3.55 (s, 3 H), 3.39 (s, 3 H), 1.83 (s, 3 H).
13C NMR (CDCl3, 100 MHz): δ = 196.9, 139.9, 114.7, 45.4, 45.0, 41.4,
21.6.
HRMS (EI): m/z calcd. for C7H13NOS: 159.0718; found: 159.0728.
Funding Information
(11) Perkowski, A. J.; Cruz, C. L.; Nicewicz, D. A. J. Am. Chem. Soc.
2015, 137, 15684.
We thank the foundation support from National Natural Science
Foundation of China (21302150), Hubei Provincial Department of Ed-
ucation (D20131501), Scientific Research Foundation for the Re-
turned Overseas Chinese Scholars, State Education Ministry
[2012]1707, foundation of Chutian distinguished fellow from Hubei
Provincial Department of Education, foundation of High-end Talent
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Acknowledgment
We thank Prof. Aiwen Lei at Wuhan University for his generous NMR
analysis support.
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Supporting Information
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J. Sulfur Chem.; 2017, DOI: 10.1080/17415993.2017.1337771.
(23) Chang, C. Z.; Xu, W.; Zeng, M. T.; Liu, M.; Liu, X.; Zhu, H.; Dong,
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Supporting information for this article is available online at
https://doi.org/10.1055/s-0036-1588545.
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–E