Tipos de túneles

To a solution of 1 (2.00 g, 20.0 mmol) in hydrocholric acid (2 M, 50 mL) at 70 C was added ammonium dichromate (2.52 g, 10.0 mmol) and stirred for an hour. After cooling the deep blue solution a colorless precipitate was filtered and washed with ethanol and diethylether, yielding 0.42 g (vii).

IR: = 3398 (vs), 3178 (s), 3085 (s), 3020 (s), 2977 (s), 1690 (vs), 1671 (vs), 1582 (vs), 1520 (vs), 1470 (vs), 1436 (s), 1412 (vs), 1351 (m), 1301 (s), 1209 (m), 1145 (m), 1086 (w), 1049 (w), 1021 (w), 1003 (w), 981 (m), 970 (m), 897 (w), 819 (w), 762 (m), 740 (m), 710 (m), 679 (w), 628 (w) cm–1_. 1_{H NMR (DMSO-D6): δ= 2.63 (s, 3H), 7.06 (br, 1H), 8.36 (s, 2H),}

References 9.61 (s, 1H) ppm. 13_{C NMR (DMSO-D6): δ= 13.9, 154.2, 154.6, 157.9, 162.0, 171.9 ppm.} 14_{N NMR (DMSO-D6): δ= 1 ppm. MS (DEI}+ _{): m/z = 98.1 (20), 181.1 (100). Elemental}

analysis: found: C 31.06; H 3.70; N 48.36.

4.4.7 OXIDATION WITH BROMINE (VIII)

To a suspension of 1 (2.00 g, 20.0 mmol) in water (20 mL) was carefully added bromine (1.0 mL, 20 mmol) at 0°C. The vessel with reaction mixture was closed and stirred for one hour at 0°C and two hours at room temperature. Then the flask was opened and stirred over night at room temperature. The solvent was evaporated and the residue recrystallized from little water The obtained precipitate was washed with ethanol and dieethylether to yield 0.05g of a yellow powder (viii).

IR: = 3442 (m), 3256 (m), 3179 (s), 2176 (w), 1675 (vs), 1584 (m), 1513 (s), 1401 (s), 1344 (m), 1112 (w), 975 (w), 931 (w), 794 (w), 770 (w), 672 (w) cm−1_. 1_{H NMR (DMSO-D6): δ=}

8.37 (s) ppm. 13_{C NMR (DMSO-D6): δ= 172.7, 175.2 ppm. MS (DEI}+ _{): m/z = 112.1 (54),} 125.1 (92), 196.1 (24). Elemental Analysis: found: C 24.46; H 3.36; N 49.42.

5

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