Publication
Reaction of pyrroles with ethyl 2-nitroso- and 2-azo-propenoates, and with ethyl cyanoformate N-oxide: a comparison of the reaction pathways
| dc.contributor.author | Gilchrist, Thomas L. | |
| dc.contributor.author | Lemos, A. | |
| dc.date.accessioned | 2012-03-09T16:03:48Z | |
| dc.date.available | 2012-03-09T16:03:48Z | |
| dc.date.issued | 1993 | |
| dc.date.updated | 2012-02-27T17:45:53Z | |
| dc.description.abstract | The reaction of ethyl 2-nitrosopropenoate 2a with 1 -methylpyrrole, 2.5-dimethylpyrrole and 2.5- diphenylpyrrole has been investigated. In every case the products result from highly regioselective attack at C-2 of the pyrrole by the electrophile. The azopropenoate esters 2b and 2c react similarly with pyrroles, to the extent that even 1 -(triisopropylsilyl)pyrrole is attacked exclusively at the 2-position by the azo ester 2b. In contrast, the nitrile oxide ethyl cyanoformate N-oxide 12 reacts at the 3-position of 2.5- dimethyl- and of 2,5-diphenyl-pyrrole. The reactions of the nitroso and azo esters with pyrroles are interpreted as Diels-Alder cycloadditions with inverse electron demand. | por |
| dc.identifier.citation | Journal of the Chemical Society, Perkin Transactions 1, 13, 1391-1391, 1993. | por |
| dc.identifier.issn | 0300-922X | |
| dc.identifier.other | AUT: ALE01411; | |
| dc.identifier.uri | http://hdl.handle.net/10400.1/936 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.subject | Diels-Alder | por |
| dc.subject | Heterocycles | por |
| dc.subject | azoalkene | por |
| dc.title | Reaction of pyrroles with ethyl 2-nitroso- and 2-azo-propenoates, and with ethyl cyanoformate N-oxide: a comparison of the reaction pathways | por |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.title | Journal of the Chemical Society. Perkin transactions 1 | |
| person.familyName | Lemos | |
| person.givenName | Americo | |
| person.identifier.ciencia-id | A81D-6DC7-31E4 | |
| person.identifier.orcid | 0000-0001-9588-4555 | |
| person.identifier.rid | B-4892-2008 | |
| person.identifier.scopus-author-id | 11139694000 | |
| rcaap.rights | openAccess | por |
| rcaap.type | article | por |
| relation.isAuthorOfPublication | 70dfe028-027a-4dec-b6e3-1a49c9be9e60 | |
| relation.isAuthorOfPublication.latestForDiscovery | 70dfe028-027a-4dec-b6e3-1a49c9be9e60 |