S. Gmouh et al. / Tetrahedron 56 (2000) 8361±8366
8365
pressure evaporation of the combined aqueous phases
yielded a brown gum from which 1H NMR analysis proved
References
ammonium 67 to be the major product.
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È
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1
1250, 1190; H NMR: d 8.97±8.94(m, 2H), 7.85±7.7(m,
4H), 7.54±7.42(m, 8H), 3.25(s, 3H); 13C NMR: d 185.07,
166.69, 135.18, 134.49, 131.88, 130.97, 129.85, 129.30,
128.21, 127.09, 126.30, 125.39, 26.15; EIMS 295 [M1],
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77; HRMS calc. For C22H17N: 295.1361. Found 295.1295.
N,N-dimethyl bisnaphthylmethylidenammonium iodide
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overnight. After cooling, the solid was collected by ®ltration
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1
7. Data for compound 6: mp.2608C (dec); [a]2D0210 (c 1,
1190; H NMR: d 8.34±8.28(m, 2H), 8.15±7.98(m, 4H),
7.78±7.51(m, 8H), 4.058(s, 3H), 4.045(s, 3H); 13C NMR:
d 135.27, 134.67, 134.15, 133.92, 132.21, 131.43, 130.7,
130.3, 130.09, 129.43, 128.76, 128.12, 126.27, 125.83,
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3.18.
1
CH3OH); H NMR: d 4.05 (m, 3H), 3.49 (s, 6H), 3.2 (m, 3H),
2.1 (m, 4H); 13C NMR: ( 67.9, 63.4, 59.02, 51.4, 51.5, 27.9, 23.,
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PTC alkylation procedure
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dissolved in the organic solvent (5 ml) and to this solution
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Acknowledgements
Â
This joint program was made possible thanks to the Comite
12. (a) Hanquet, G.; Lusinchi, X.; Milliet, P. Tetrahedron Lett.
1988, 29, 3941±3944. (b) Hanquet, G.; Lusinchi, X. Milliet, P.
Mixte Inter Universitaire Franco-Marocain (A.I. 185/SM/
99). We thank Yves Dat, from the University of Caen, for
the HMRS analysis.
Â
C. R. Acad.Sci. Paris 1991, 313, 625±628. (c) Bohe, L.; Hanquet,
G.; Lusinchi, M.; Lusinchi, X. Tetrahedron Lett. 1993, 34,