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Cover Picture: Solvent‐Dependent Competitive Rearrangements of Cyclic Tertiary Propargylamine N ‐Oxides (Eur. J. Org. Chem. 4/2004)
Author(s) -
Szabó Anna,
GalambosFaragó Ágnes,
Mucsi Zoltán,
Timári Géza,
VasváriDebreczy Lelle,
Hermecz István
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200490008
Subject(s) - chemistry , cover (algebra) , transition state , ab initio , aldehyde , computational chemistry , oxide , kinetic energy , solvent , reaction mechanism , ab initio quantum chemistry methods , organic chemistry , catalysis , molecule , mechanical engineering , physics , quantum mechanics , engineering
The cover picture shows the energy profile calculated by ab initio methods of the competing reactions from N ‐propargylmorpholine N ‐oxide in protic medium: the well‐known Meisenheimer rearrangement to O ‐allenylhydroxylamine and the recently revealed rearrangement to enamino aldehyde. Kinetic measurements in different alcohols, in agreement with the ab initio studies, afforded information on the structures of the transition states involved in the rate‐determining and product‐distribution‐determining steps, supporting our assumption on the mechanism of these reactions. Details are discussed in the article by I. Hermecz et al. on p. 687 ff.