Addition and correction
Four-fold click reactions: Generation of tetrahedral methane- and adamantane-based building blocks for higher-order molecular assemblies
Oliver Plietzsch, Christine Inge Schilling, Mariyan Tolev, Martin Nieger, Clemens Richert, Thierry Muller and Stefan Bräse
Org. Biomol. Chem., 2009, 7, 4734–4743 (DOI: 10.1039/B912189G). Amendment published 14th December 2011.
There was an
omission in the experimental procedure for tetrakis(4-azidophenyl)methane
(7). The corrected procedure is given below with the additional text in
bold.
Tetrakis(4-azidophenyl)methane (7). 4,4′,4′′,4′′′-Methanetetrayltetraaniline
(5) (1.50 g, 3.93 mmol, 1.0 equiv.) was
suspended in water (30 mL) and the reaction mixture
was cooled to –5 °C. At
this temperature conc. sulfuric acid (15 mL) and a solution of sodium nitrite (1.23 g,
17.7 mmol, 4.5 equiv.) in
water (9 mL) were added slowly and the suspension
turned to a dark clear solution. Then, a solution of sodium azide
(1.23 g, 17.7 mmol, 4.5 equiv.) in water (9 mL) was added dropwise under a
strong evolution of gas. Caution: sodium azide
is potentially explosive. Furthermore, the evolution of hydrazoic
acid is possible under acidic conditions. The reaction mixture was stirred
for 2 h at room temperature. After this, the formed precipitate was filtered
off, washed with water (100 mL) and dried in vacuo to give tetrakis(4-azidophenyl)methane
(7) (1.43 g, 75%) as a grey solid. Rf
0.30 (cyclohexane/EtOAc
25:1); δH
(400 MHz; CDCl3) 6.86 (8 H, d, J 8.8, Arm-H),
7.06 (8 H, d, J 8.8, Aro-H) ppm; δC
(100 MHz; CDCl3) 63.3 (Cq(Ar)4), 118.4 (+, Co-Ar), 132.1 (+, Cm-Ar),
138.2 [Cq-Ar(N3)], 142.9
[Cq-Ar(C)] ppm;
ν/cm-1 (DRIFT)
3032wv, 2544vw, 2412vw, 2252w, 2124s, 1601m, 1577w, 1501s, 1413w, 1290s, 1192
m, 1130w, 1119w, 1017w, 945vw, 911vw, 829m, 757vw, 701vw, 671w, 634vw, 555m,
538m, 414vw; m/z (EI) 484 (M+, 100%), 456 (35), 317 (M+
– 12N, 12), 240 (M+ – C6H4N12, 9);
C25H16N12 calcd.
484.1621; found 484.1623 [M+].
The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.
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