Anthracenic and naphthalenic vic-diepoxides. A new kind of isomerization going through fragmentation

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2267-2270

  Rigaudy, Jean ^a   Lachgar, Mohamed ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOMERISM; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00294-3     Document Type: Article

References (11)

1. 1. Rigaudy, J.; Maurette, D.; Kim Cuong, N. Comptes rendus Acad, Sci. 1971, 273, 1553-1556.
2. 2. Rigaudy, J.; Caspar, A.; Lachgar, M.; Maurette, D.; Chassagnard, C. Bull. Soc. Chim. Fr. 1992 129, 16-24.
3. 3. Rigaudy, J.; Lachgar, M.; Saad, M. Bull. Soc. Chim. Fr. 1994, 131, 177-187.
4. 4. Rigaudy, J.; Lachgar, M.; Caspar, A.; Chassagnard, C. Bull. Soc. Chim. Fr. 1996, 133, 481-490.
5. 2=), 125.5 to 127.7 (6 CH arom.), 133.1 to 133.4 (4 C quat.arom.), 151.2 (C-1); EIMS (70 eV) m/z, (r.i.): 266 (87), 248 (25), 223 (100).
6. 6. Epoxy-ketone 4b has been previously obtained by photoisomerization of the corresponding diepoxide 2b; under acidic treatment, it gives a mixture of 10b and 11b (see Ref 3). One can then deduce the transient formation of epoxy-ketone 4b from 2b in experiment 4. (figure presented)
7. 7. Fieser, L.F.; Fieser, M. in Reagents for Organic Chemistry, Wiley and Sons Ed 1967, Vol. 1, p.629.
8. 4 (in benzene) has been formerly found to effect a rapid rearrangement to carbonyl derivatives of epoxides involving a tertiary center, see: Rickborn, B. and Gerkin, R J. Am. Chem. Soc. 1971, 93, 1693-1700.
9. 3); EIMS (70 eV) m/z (r.i.) 216 (1), 173 (100).
10. 10. - Breitmaier, E.; Voelter, W. in Carbon-13 NMR Spectroscopy, VCH Ed, 3rd Edition 1987, p. 215.
11. 11. - Grob, C-A.; Angew. Chem. Int. Ed. 1967, 6, 1-15.