The Journal of Organic Chemistry

Nucleophilic substitution at an acetylenic carbon. Kinetics, mechanism, and syntheses with tertiary amines

JI Dickstein, SI Miller

Index: Dickstein,J.I.; Miller,S.I. Journal of Organic Chemistry, 1972 , vol. 37, # 13 p. 2175 - 2180

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Citation Number: 6

Abstract

Haloalkynes cleave one bond at the amine bridgehead to produce ynamines 9 or amides 10. A number of new substitution products have been obtained with phenylbromo-or phenylchloroacetylene and 1, 4-diazobicyclo [2.2. 2] octane (Dabco), brucine, dihydrobrucine, quinuclidine, as well as with 2 '-(3-chloro-1, l-dimethyl-2-propyny1oxy) tetrahydropyran and Dabco. Rate data for the second-order reactions of several halides ...