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| Title: | Radical β-fragmentation of bicyclo[3.3.0]-carbinolamides: Synthesis of five- and eight-membered cyclic imides |
Authors: | Hernández, Rosendo CSIC; Melián, Daniel; Prangé, Thierry; Suárez, Ernesto CSIC ORCID | Issue Date: | 1995 | Publisher: | Elsevier | Citation: | Heterocycles 41(3): 439-454 (1995) | Abstract: | The influence of 4-alkyl or 4-aryl substituents in the regioselectivity of the β-fragmentation of carbinolamidyl radicals generated from the corresponding carbinolamides (7-13) by irradiation with visible light in the presence of (diacetoxyiodo)benzene and iodine is described. In the case of the less hindered carbinolamides 1-hydroxyazabicyclo[3.3.0]octan-3-one (7) and 4-(2'-phenylethyl)-1-hydroxyazabicyclo[3.3.0]octan-3-one (8) important amounts of 8-membered cyclic imides were obtained together with the expected 5-membered imides (succinimides). | Description: | 16 pages, 1 figure, 1 table, 2 schemes. | Publisher version (URL): | http://linkinghub.elsevier.com/retrieve/pii/0385541495940565 | URI: | http://hdl.handle.net/10261/17240 | ISSN: | 0385-5414 |
| Appears in Collections: | (IPNA) Artículos |
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