Artículo
Ponce, M.A.; Ramirez, J.A.; Galagovsky, L.R.; Gros, E.G.; Erra-Balsells, R. "Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement" (2000) Journal of the Chemical Society. Perkin Transactions 2(11):2351-2357
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Abstract:
The course of the singlet-oxygen ene reaction with stigmasta-5,22-dienes may be controlled if in the substrate a good leaving group as substituent is present at 3-C. Thus when the 5α-hydroperoxystigmasta-5,22-diene is formed instead of the well known allylic rearrangement to yield the 7α-hydroperoxystigmasta-5,22-diene isomer an intramolecular nucleophilic substitution can then occur yielding 5α-hydroxystigmasta-6,22-dien-3-one. Various stigmasta-5,22-dienes were chosen to elucidate which feature of the stigmastane is necessary to control the course of the reaction. Thus, 3β-F, 3β-Cl, 3β-Br, 3β-I and 3α-Br-stigmasta-5,22-dienes were firstly prepared and fully characterized in order to study their reaction with 1O2 under different experimental conditions. 3β-Acetoxy- and 3β-mesyloxy-stigmasta-5,22-diene derivatives were also prepared and studied.
Registro:
| Documento: | Artículo |
| Título: | Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement |
| Autor: | Ponce, M.A.; Ramirez, J.A.; Galagovsky, L.R.; Gros, E.G.; Erra-Balsells, R. |
| Filiación: | Departamento de Quimica Organica, Facultad Ciencias Exactas Naturales, Universidad de Buenos Aires, Pabellon II, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| Palabras clave: | Derivatives; Isomers; Light absorption; Molecular structure; Nuclear magnetic resonance spectroscopy; Photochemical reactions; Substitution reactions; Hydroperoxystigmastadiene; Intramolecular nucleophilic substitution; Photosensitized oxidation; Organic compounds |
| Año: | 2000 |
| Número: | 11 |
| Página de inicio: | 2351 |
| Página de fin: | 2357 |
| Título revista: | Journal of the Chemical Society. Perkin Transactions 2 |
| Título revista abreviado: | J Chem Soc Perkin Trans 2 |
| ISSN: | 03009580 |
| CODEN: | JCPKB |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n11_p2351_Ponce |
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Citas:
---------- APA ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G. & Erra-Balsells, R. (2000) . Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement. Journal of the Chemical Society. Perkin Transactions 2(11), 2351-2357.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n11_p2351_Ponce [ ]
---------- CHICAGO ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. "Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement" . Journal of the Chemical Society. Perkin Transactions 2, no. 11 (2000) : 2351-2357.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n11_p2351_Ponce [ ]
---------- MLA ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. "Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement" . Journal of the Chemical Society. Perkin Transactions 2, no. 11, 2000, pp. 2351-2357.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n11_p2351_Ponce [ ]
---------- VANCOUVER ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. Singlet-oxygen ene reaction with 3β-substituted stigmastanes. An alternative pathway for the classical Schenck rearrangement. J Chem Soc Perkin Trans 2. 2000(11):2351-2357.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n11_p2351_Ponce [ ]
