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Type: Artigo de periódico
Title: Gas-phase Chemistry Of Acylium Ions, Seven-to-five Ring Contraction Of 1,3-dioxepane And 1,3-dioxep-5-ene
Author: Moraes L.A.B.
Kotiaho T.
Eberlin M.N.
Abstract: As shown by pentaquadrupole triple-stage mass spectrometric and 18O-labeling experiments, two seven-membered cyclic acetals, 1,3-dioxepane and 1,3-dioxep-5-ene, fail to react by transacetalization with the gaseous acylium ions CH3C+=O and (CH3)2NC+=O. Instead, a novel and less exothermic but more kinetically favored reaction, seven-to-five ring contraction, occurs predominantly, and to great extents with the most reactive acylium ion, (CH3)2NC+=O. 1,3-Dioxepane yields O-acylated tetrahydrofurans; 1,3-dioxep-5-ene yields O-acylated 2,5-dihydrofurans.
Rights: fechado
Identifier DOI: 10.1002/(SICI)1096-9888(199906)34:6<670::AID-JMS819>3.0.CO;2-H
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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