Elimination reactions of hydrazonium salts: experimental and theoretical evidence for a large stereoelectronic effect of nitrogen

NM Tho, LF Clarke, AF Hegarty

Index: Nguyen, Minh Tho; Clarke, Leo F.; Hegarty, Anthony F. Journal of Organic Chemistry, 1990 , vol. 55, # 25 p. 6177 - 6183

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Citation Number: 17

Abstract

Elimination of trimethylamine from hydrazonium salts (8, R= Me) is promoted by base (methoxide ion in methanol). The mechanism is characterized as E2 as shown by substituent effects (p=+ 2.57), Br0nsted coefficients, a primary kinetic isotope effect (kH/kD= 2.10), and solvent effects. Variation in the leaving group (8, R= arylmethyl) shows that NN bond cleavage is leas well advanced in the transition state than CH bond breaking. The ...

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