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Diazotization
of Amines 2 - General Procedure
To a stirred
solution of amines 2 (1.0 mmol) and HBF4 (54% in
Et2O. 1.2 mmol. 1.90 g) in HCOOH (15 mL), at 5-10 ˚C, 3-methylbutyl
nitrite (1.29 g, 1.1 mmol) was slowly added at such a rate that
the temperature did not exceed 10 ˚C. Then the
reaction mixture was stirred for 10 min in an ice bath, and at r.t.
for 5 min. Finally, after cooling at 0-5 ˚C,
anhyd Et2O was added to precipitate salts 3,
gathered by filtration on a Büchner funnel, and washed
several times with Et2O. After drying under vacuum, pure
salts 3 were obtained and immediately reacted
(physical and ¹H NMR and ¹³C
NMR spectral data identical to literature).
Conversion
of Crude Salts 3 to
O
-Ethyl
S
-Aryl Dithiocarbonates 4 and Oxidative Chlorination
of Crudes 4 to Arenesulfonyl Chlorides 5 - General Procedures
Crude
salts 3 (1.0 mmol) were carefully added
under stirring to a solution of potassium O-ethyl
dithiocarbonate (1.0 mmol, 1.60 g) and Na2CO3 (1.0
mmol, 1.06 g) in H2O (40 mL), heated to 35-40 ˚C.
Then the reaction mixture was stirred at 60 ˚C
for 20 min. After cooling to r.t., the resultant mixture was poured
into Et2O-H2O (40 mL, 2:1). The aqueous
layer was separated and extracted with Et2O (2 × 20 mL).
The combined organic extracts were washed with H2O (20
mL), dried over Na2SO4, and evaporated. The
crude residues were directly reacted to give arenesulfonyl chlorides 5. A small stream of Cl2 was
bubbled through a well-stirred ice-cooled emulsion of crudes 4 in H2O (20 mL) or HCOOH-H2O
(40 mL, 9:1; for crude 4f), at such a rate that
the temperature did not rise to 10 ˚C. The reaction
was stopped when Cl2 was no longer absorbed and TLC analysis (PE-Et2O,
8:2) showed the presence of only one persistent spot. After removing
chlorine excess, the reaction mixture was extracted with CH2Cl2 (3 × 20
mL); organic extracts were neutralized with 10% aq NaHCO3,
dried, and evaporated under reduced pressure. Crude residues chromatographed
on a short column (PE-Et2O, 9:1) provided pure
arenesulfonylchlorides 5 (comparison with literature
data or commercially pure samples).
Benzene-1,2-disulfonyl
Chloride (5f)
²g
After completion of oxidative
chlorination (TLC analysis and appearance of a fine dispersed white
solid), chlorine excess was removed under vacuum; crude virtually
pure 5f was filtered on a Büchner
funnel and washed with cold H2O. Mp 143-144 ˚C
(CCl4; lit. 143-144 ˚C).²f ¹H
NMR (200 MHz, CDCl3): δ = 8.04-8.11
(m, 2 H), 8.45-8.53 (m, 2 H). ¹³C
NMR (50 MHz, CDCl3): δ = 132.6
(2 C), 136.4 (2 C), 141.4 (2 C). MS (EI): m/z (%) = 274
(20) [M+].
Biphenyl-2,2′-disulfonyl Chloride (7)
Mp
143-144 ˚C (CHCl3-PE;
lit. 144-145 ˚C).²³ Prepared
by suspending crude 17 in CH2Cl2/H2O
(10 mL, 10:1) and reacting with excess chlorine at 0-10 ˚C
for 30 min; then HCOOH (10 mL) was added, and chlorination was continued
until only two persisting spots were present on TLC analysis. By
column chromatography (CH2Cl2-MeOH, 99:1),
disulfonyl chloride 7 was eluted as first
product (R
f
= 0.8);
the second eluted product was 13 (R
f
= 0.3);
mp 143-144 ˚C (CHCl3-PE;
lit.²³ 144-145 ˚C). ¹H
NMR (200 MHz, CDCl3): δ = 7.49
(dd,, J = 1.8,
7.2 Hz, 1 H), 7.67 (td, J = 1.8, 7.6
Hz, 1 H), 7.75 (td, J = 1.6,
7.6 Hz, 1 H), 8.20 (dd, J = 1.6, 8.0
Hz, 1 H). ¹³C NMR (50 MHz, CDCl3): δ = 129.0
(2 C), 129.8 (2 C),132.0 (2 C), 134.3 (2 C), 135.7 (2 C), 142.6
(2
C).
(
R
)-Binaphthyl-2,2′-disulfonyl Chloride
(8)
Colorless needles; mp 241.2-242.2 ˚C
(CHCl3-PE; lit. 244.3 ˚C).³b ¹H
NMR (200 MHz, CDCl3): δ = 7.09
(d, J = 8.6
Hz, 2 H), 7.38 (ddd, J = 1.4,
7.0, 8.6 Hz, 2 H), 7.65 (ddd, J = 1.2,
7.0, 8.2 Hz, 2 H), 8.00 (d, J = 8.4
Hz), 8.20 (d, J = 9.0
Hz, 2 H), 8.27 (d, J = 9.0
Hz, 2 H). ¹³C NMR (50 MHz, CDCl3): δ = 123.2
(2 C), 127.9 (2 C), 128.4 (2 C), 128.5 (2 C), 130.1 (2 C), 131.0
(2 C), 131.8 (2 C), 133.6
(2 C), 135.3 (2 C), 140.7 (2
C).