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Helvetica Chimica Acta ± Vol. 88 (2005)
(2 Me); 24.3 (CH); 46.9 (2 CH2); 155.8 (quart. C). Anal. calc. for C9H17F3N4O3S (318.3): C 33.96, H 5.38, N
17.60; found: C 33.87, H 5.33, N 17.84.
7.4. 1,4-Diethyl-4,5-dihydro-5-(2-methylethylidene)-1H-tetrazole (21).
A suspension of 20 (10.0 g,
31.4 mmol) and NaH (1.64 g, 68 mmol) in dry Et2O (100 ml) was stirred until the gas evolution had ceased
(17 h). Distillation of the solvent i. v. and of the yellow oily residue at 40 ± 508 (bath temp.)/10À3 Torr in a short-
path distillation apparatus (condenser at À 208) afforded 21 (3.11 g, 59%). Yellow oil which was kept at low
temp. under dry Ar. 1H-NMR (CDCl3, 200 MHz): 1.14 (t, J 7.0, 6 H); 1.72 (s, 6 H); 3.85 (q, J 7.0, 4 H).
13C-NMR (CDCl3, 50 MHz): 13.4 (2 Me); 19.8 (2 Me); 45.1 (2 CH2); 67.1 (quart. C); 133.9 (quart. C).
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