Heteropoly acids in Ritter reaction
Russ.Chem.Bull., Int.Ed., Vol. 55, No. 2, February, 2006
389
MS (EI, 70 eV), m/z (Irel (%)): 257 [M]+ (24); 173 (1); 136 (16);
121 (21); 105 (100); 95 (27); 77 (58); 67 (9); 51 (12); 41 (21).
13C NMR (DMSO—CCl4), δ: 49.2 (C(1)); 56.4 (C(2)); 36.3
(C(3)); 44.3 (C(4)); 26.8 (C(5)); 35.4 (C(6)); 46.3 (C(7)); 19.7,
20.3 (2 CH3, CH3C(7)); 11.3 (CH3, CH3C(1)); 127.1, 127.4,
130.1(Co, Cp, Cm); 135.4 (Cipso); 166.8 (CO, COPh).
124.9, 125.5, 125.8, 126.2, 127.9, 129.2, 129.9, 133.0, 135.3
(10C, C10H7); 168.4 (CO, COC10H7).
We are grateful to A. A. Michurin for providing samples
of nitriles 1b—e.
Nꢀ(1,7,7ꢀTrimethylnorbornyl)acrylamide (3c) was obtained
by heating a mixture of acrylonitrile (1c) (3 mL), camphene (2)
(0.09 g, 0.7 mmol), water (0.2 mL, 11.1 mmol), and H3PW12O40
(1 g, 0.3 mmol) at 80 °C for 6 h; m.p. 132 °C (from
C6H14—AcOEt (4 : 1 v/v); cf. Ref. 6: m.p. 133 °C).
References
1. J. J. Ritter and P. P. Minieri, J. Am. Chem. Soc., 1948,
70, 4045.
2. E. N. Zil´berman, Reaktsii nitrilov [Reactions of Nitriles],
Khimiya, Moscow, 1972, p. 251 (in Russian).
3. S. A. Kazakov, O. A. Kazantsev, and A. P. Malyshev,
Zh. Prikl. Khim., 2002, 75, 2066 [J. Appl. Chem., 2002, 75
(Engl. Transl.)].
4. I. V. Kozhevnikov, Usp. Khim., 1987, 56, 1417 [Russ. Chem.
Rev., 1987, 56 (Engl. Transl.)].
5. I. V. Kozhevnikov, Usp. Khim., 1993, 62, 510 [Russ. Chem.
Rev., 1993, 62 (Engl. Transl.)].
6. T. Sasaki, S. Eguchi, and T. Oyobe, Bull. Chem. Soc. Jpn,
1970, 43, 1252.
7. C. W. Roberts and M. L. Maskaleris, J. Org. Chem., 1959,
24, 926.
Nꢀ(1,7,7ꢀTrimethylnorbornyl)propionamide (3d) was obtained
by heating a mixture of propionitrile (1d) (10 mL), camphene
(2) (0.3 g, 2.2 mmol), water (0.7 mL, 38.9 mmol), and
H3PW12O40 (3.13 g, 1.1 mmol) at 65 °C for 8 h; m.p. 100 °C
(from C6H14). Found (%): C, 74.76; H, 11.02; N, 6.70.
C13H23NO. Calculated (%): C, 74.64; H, 11.00; N, 6.69.
MS (EI, 70 eV), m/z (Irel (%)): 209 [M]+ (15); 166 (2); 136 (19);
121 (21); 108 (8); 95 (84); 79 (18); 67 (33); 57 (86); 41 (100).
13C NMR (DMSO—CCl4), δ: 48.4 (C(1)); 55.5 (C(2)); 37.1
(C(3)); 44.2 (C(4)); 26.7 (C(5)); 35.5 (C(6)); 46.2 (C(7));
20.2, 20.2 (2 CH3, CH3C(7)); 11.1 (CH3, CH3C(1)); 28.3
(CH2, CH3CH2CO); 22.3 (CH3, CH3CH2CO); 172.2 (CO,
CH3CH2CO).
8. J. Sasaki, S. Eguchi, and K. Shoji, J. Chem. Soc. (C),
1969, 406.
9. R. M. Carman and K. L. Greenfield, Austr. J. Chem., 1984,
37, 1785.
Nꢀ(1,7,7ꢀTrimethylnorbornyl)ꢀ1ꢀnaphthamide (3e) was obꢀ
tained by heating a mixture of 1ꢀnaphthonitrile (1e) (1.5 g),
camphene (2) (0.5 g, 3.6 mmol), water (1 mL, 55.5 mmol), and
H3PW12O40 (0.41 g, 0.1 mmol) at 92 °C for 6 h; m.p. 121 °C
(from C6H14—AcOEt (2 : 1 v/v)). Found (%): C, 82.21; H, 8.16;
N, 4.57. C21H25NO. Calculated (%): C, 82.08; H, 8.14; N, 4.56.
MS (EI, 70 eV), m/z (Irel (%)): 307 [M]+ (35); 264 (5); 238 (4);
184 (5); 172 (11); 155 (100); 127 (89); 109 (5); 95 (18); 55 (14);
41 (27). 13C NMR (DMSO—CCl4), δ: 49.4 (C(1)); 56.6 (C(2));
36.4 (C(3)); 44.4 (C(4)); 26.9 (C(5)); 35.7 (C(6)); 46.4 (C(7));
19.8, 20.4 (2 CH3, CH3C(7)); 11.7 (CH3, CH3C(1)); 124.6,
10. Organikum.
Organischꢀchemisches
Grundpraktikum,
Deutscher Verlag der Wissenschaften, Berlin, 1976.
11. Spravochnik khimika [A Chemist´s Handbook], Khimiya,
Moscow, 1964, vol. 2, p. 704 (in Russian).
Received July 15, 2005;
in revised form November 22, 2005