[N-(o-Nitrophenylsulfonyl)imino]phenyliodinane. Iodobenz-
ene diacetate (3.22 g; 1.0 mmol) was added to a stirred
mixture of potassium hydroxide (1.4 g; 0.025 mmol) and
o-nitrobenzenesulfonamide (2.02 g; 1.0 mmol) in HPLC grade
methanol (40 mL), keeping the temperature at 0 ЊC during the
addition. The solution was stirred at room temperature and
over a 4 hour period a cream precipitate formed. The precipi-
tate was then filtered, washed with distilled water and dried
at room temperature in a vacuum desiccator (2.41 g, 59.6%). δH
(d6-DMSO, 400 MHz) 7.6–7.9 (m), 7.5 (m, 1H), 7.4 (m, 2H).
Anal. cald. C 35.69, H 2.27, N 6.93; Found C 35.61, H 2.24, N
6.75%.
triflate in dry acetonitrile prior to the addition of the styrene
and nitrene donor. Reaction time varied according to the differ-
ent nitrene precursor. The reaction was stirred in air at 25 ЊC
until complete dissolution of the nitrene donor. The reaction
mixture was then filtered through a plug of silica with ethyl
acetate (50 cm3) as eluent. Flash chromatography gave the
aziridine as a white solid. Experiments were carried out in
triplicate and reproducible results are reported.
Heterogeneous aziridine reaction catalysed by CuHY
Styrene (0.101 g, 1.0 mmol), nitrene donor (1.5 mmol) and
CuHY (0.3 g) were stirred together in dry acetonitrile (2.5 cm3)
at 25 ЊC. If a chiral bis(oxazoline) (0.07 mmol, Aldrich, 98%)
was added, this was stirred with the CuHY in the acetonitrile
prior to the addition of the styrene and nitrene donor. Reaction
times varied depending on the nitrene donor. The reaction
mixture was stirred in air at 25 ЊC until complete dissolution of
the nitrene donor. The reaction mixture was then filtered
through a plug of silica with ethyl acetate (50 cm3) as eluent.
Flash chromatography gave the aziridine as a white solid.
Experiments were carried out in triplicate and reproducible
results are reported.
[N-(p-Methoxyphenylsulfonyl)imino]phenyliodinane.
Iodo-
benzene diacetate (3.22 g; 1.0 mmol) was added to a stirred
mixture of potassium hydroxide (1.4 g; 0.025 mmol) and
p-methoxybenzenesulfonamide (1.87 g; 1.0 mmol) in HPLC
grade methanol (40 mL), keeping the temperature at 0 ЊC
during the addition. The solution was stirred at room temper-
ature and over a 4 hour period a cream precipitate formed. The
precipitate was then filtered, washed with distilled water and
dried at room temperature in a vacuum desiccator (2.58 g,
66.3%). δH (d6-DMSO, 400 MHz) 7.7 (m, 2H), 7.35 (m, 4H),
6.7 (d, 2H), 3.7 (s, 3H). Anal. cald. C 40.1, H 3.08, N 3.59;
Found C 40.15, H 3.18, N 3.55%.
Acknowledgements
We thank Synetix and the EPSRC for funding.
[N-(Phenylsulfonyl)imino]phenyliodinane. Iodobenzene di-
acetate (3.22 g; 1.0 mmol) was added to a stirred mixture of
potassium hydroxide (1.4 g; 0.025 mmol) and benzenesulfon-
amide (1.57 g; 1.0 mmol) in HPLC grade methanol (40 mL),
keeping the temperature below 10 ЊC during the addition. The
resulting clear yellow solution was stirred for three hours at
room temperature and then poured into distilled water (250
mL). Over a period of 12 hours a yellow precipitate formed and
this was then filtered, washed with distilled water and dried at
room temperature in a vacuum desiccator (2.14 g, 59.6%). δH
(d6-DMSO, 400 MHz) 7–7.8 (m, 10H, aromatic protons). Anal.
cald. C 40.11, H 2.78, N 3.59; Found C 40.25, H 2.64, N 3.58%.
References
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[N-(Methylsulfonyl)imino]phenyliodinane. Iodobenzene di-
acetate (3.22 g; 1.0 mmol) was added to a stirred mixture of
potassium hydroxide (1.4 g; 0.025 mmol) and methanesulfon-
amide (1.58 g; 1.0 mmol) in HPLC grade methanol (40 mL),
keeping the temperature at 0 ЊC during the addition. The
solution was stirred at room temperature and over a 4 hour
period a cream precipitate formed. The precipitate was then
filtered, washed with distilled water and dried at room temper-
ature in a vacuum desiccator (0.94 g, 33.2%). δH (d6-DMSO,
400 MHz) 7–7.8 (m, 5H, aromatic protons), 2.6 (s, 3H). Anal.
cald. C 28.28, H 2.63, N 4.71; Found C 28.48, H 2.76, N 4.73%.
Homogeneous aziridination reactions catalysed by Cu(OTf )2
Styrene (0.101 g, 1.0 mmol), nitrene donor (1.5 mmol) and
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cm3) at 25 ЊC. If a chiral bis(oxazoline) (0.07 mmol, Aldrich,
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1722
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