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Electrophilic Reactivity of a 2-Azaallenium and of a 2-Azaallylium Ion

✍ Scribed by Guido M. Böttger; Roland Fröhlich; Ernst-Ulrich Würthwein

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 272 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1589::aid-ejoc1589>3.0.co;2-t

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✦ Synopsis

The rate constants for the reactions of the 2-azaallenium ion 1b + , the 2-azaallylium ion 2a + and the iminium ion 3 + with different nucleophiles were determined by 1 H NMR spectroscopy. By correlation with the Linear Free Enthalpy Relationship (LFER) lg k 20°C = s (E + N), developed by Mayr and Patz, the electrophilicity parameters E(1b + ) = -3.7, E(2a + ) ഠ -16 and E(3 + ) = -10.43 were obtained. They show that the relat-

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