Solvent‐Dependent Competitive Rearrangements of Cyclic Tertiary Propargylamine  N ‐Oxides | Zendy

Szabó Anna | Zendy; GalambosFaragó Ágnes | Zendy; Mucsi Zoltán | Zendy; Timári Géza | Zendy; VasváriDebreczy  Lelle | Zendy; Hermecz István | Zendy

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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)

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