Gas-phase chemistry of acylium ions: Seven-to-five ring contraction of 1,3-dioxepane and 1,3-dioxep-5-ene

Luiz Alberto B. Moraes, Tapio Kotiaho, Marcos N. Eberlin (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

11 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)670-676
JournalJournal of Mass Spectrometry
Volume34
Issue number6
DOIs
Publication statusPublished - 1999
MoE publication typeA1 Journal article-refereed

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