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Solvent‐Dependent Competitive Rearrangements of Cyclic Tertiary Propargylamine N ‐Oxides
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 - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300461
Subject(s) - chemistry , solvent , solvent effects , reaction mechanism , kinetics , ab initio , organic chemistry , medicinal chemistry , catalysis , physics , quantum mechanics
In protic media, cyclic propargylamine N ‐oxides 1 undergo solvent‐dependent competitive rearrangements leading to enamino aldehydes 5 , acrylamides 3 , and secondary amines 4 . The ratios of the products are evaluated and the possible mechanism of the competing reactions is interpreted by reaction kinetics studies and ab initio calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)