Regiospecific ring opening of N-acylaziridines by neutral hydrolysis

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6569-6570

  Besbes, Néji ^a  

^a Departement de Chimie Industrielle   (Tunisia)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; HYDROLYSIS; PH; STEREOSPECIFICITY;

EID: 0033520246     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00979-X     Document Type: Article

References (9)

1. (a) Bestes, N. Tetrahedron Lett. 1998, 39, 4275-4276.
2. (b) Buchholz, B.; Stamm, H. Isr. J. Chem. 1988, 27, 17-23.
3. (a) Heine, H. W.; Fetter, M. F.; Nicholson, E. A. J. Am. Chem. Soc. 1959, 81, 2202-2204.
4. (b) Pittmann, C. U.; McManus, S. P. J. Org. Chem. 1970, 35, 1187-1192.
5. (a) The two aziridines 1f and 1g were isomerised by the concentrated sulphuric acid into the corresponding oxazolines undergoing intramolecular O-alkylation at the C-2 carbon,
6. (b) Bestes, N. J. Soc. Alger. Chem. 1997, 7, 313-315.
7. (c) McManus, S. P.; Heam, R. A. J. Org. Chem. 1976, 41, 1895-1899.
8. Buchholz, B.; Onistchenko, A.; Stamm, H. Z. Naturforsch, B: Anorg. Chem., Org. Chem. 1986, 41, 1311-1314.
9. 13C NMR: 27.0 (q), 31.7 (t), 38.2 (t), 50.3 (t), 70.6 (s), 126.1 (d), 128.1 (d), 128.3 (d), 140.5 (s), 173.1 (s). SM m/z (%): 221 (M+, 11), 163 (100), 133 (28), 105 (65), 104 (58), 91 (93), 72 (54), 71 (44), 59 (36). Anal, calcd: C, 70.55; H, 8.64; N, 6.33; O, 14.46. Found: C, 70.68; H, 8.84; N, 6.54; O, 14.69.