The Journal of Organic Chemistry

Use of an. alpha.-fluorine substituent as a transition state probe in base-catalyzed nitrous acid eliminations

LA Kaplan, NE Burlinson

Index: Kaplan,L.A.; Burlinson,N.E. Journal of Organic Chemistry, 1972 , vol. 37, p. 3932 - 3937

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Citation Number: 4

Abstract

The results of a study of the kinetics and mechanism of the reaction of 4, 4, 4- trinitrobutyronitrile and 4, 4-dinitro-4-halobutyronitriles with base have shown that the isolated products are derived from an extremely reactive 1, l-dinitro-or 1-halo-1-nitroethylene intermediate. The a-fluorine effect has been utilized as a transition state probe to show that the mechanism by which the olefin intermediate forms is a nonreversible, second-order ...