Unexpected formation of N-(2-cyclopropenyl)phthalimides in the photosensitized decarboxylation of N-(2-cyclopropenylcarbonyloxy) phthalimides

Tetrahedron Letters

Volumn 39, Issue 9, 1998, Pages 1079-1082

  Cano, Montserrat ^a   Fabriàs, Gemma ^a   Camps, Francisco ^a   Joglar, Jesus ^a  

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PHTHALIMIDE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; DECARBOXYLATION; PHOTOSYNTHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032567881     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10732-8     Document Type: Article

References (10)

1. 1. Fabriàs, G.; Gosalbo, L.; Quintana, J.; Camps, F. J. Lipid Res. 1996, 37, 1503-1509.
2. 2. Baird, M. S.; Hopf, H.; Bushby, R. J.; Schmidt, T. Cyclopropenes: A. Synthesis; de Meijere, A., Ed.; Houben-Weyl Vol. E 17d, pp 2695-2780; Georg Thieme Verlag: Stuttgart, 1997.
3. 3. Okada, K.; Okamoto, K.; Oda, M. J. Am. Chem. Soc. 1988,110, 8736-8738.
4. 4. All compounds have been synthesized according to previously described methods. In the case of 2-cyclopropenyl carboxylic acids see, for instance: Gosalbo, L.; Barrot, M.; Fabriàs, G.; Arsequell, G.; Camps, F. Lipids 1993, 28, 1125-1130 and references cited therein. N-(2-cyclopropenylcarbonyloxy)phthalimides were prepared from the corresponding 2-cyclopropenyl carboxylic acids and N-hydroxyphthalimide as described in reference 3.
5. 32S: C, 74.93; H, 12.58; S, 12.50. Found: C, 74.69; H, 12.67; S, 12.41.
6. 6. Two control experiments were carried out by irradiation of 1 with no sensitizer neither radical donor or only with sensitizer. In both experiments the starting material was recovered unchanged.
7. 1H-NMR in the crude reaction, but isolation of 4 in pure state was unsuccessful (Scheme 2. Table 1, entries 4 and 5).
8. 2: C, 77.14; H, 8.09; N, 4.50. Found: C, 77.12; H, 8.28; N, 4.34.
9. 9. Under these thermal conditions the reaction time has to be prolonged.
10. 2: C, 76.45; H, 12.83. Found: C, 76.26; H, 12.79.