FORMATION AND ISOMERIZATION OF 2-AZAALLYLLITHIUM REAGENTS IN DEPROTONATIONS OF N-BENZYL KETIMINES CONTAINING ALPHA-PROTONS Academic Article uri icon

abstract

  • Deprotonation of the N-benzylimine of 3-pentanone by lithium diisopropylamide (LDA) in tetrahydrofuran occurs at the benzylic position to give a 2-azaallyllithium reagent in high yield. On standing, the 2-azaallyllithium reagent isomerizes to a 1-azaallyllithium reagent. The N-benzylimine of 2-butanone can be similarly deprotonated by LDA at the benzylic position in competition with deprotonation at the -positions to give a 2-azaallyllithium reagent in up to 22% yield. The N-benzylimine of acetone is not appreciably deprotonated at the benzylic position by LDA. Kinetic studies of the isomerization of 2-azaallyl- to 1-azaallyilithium reagent from the 3-pentanone imine suggest that this reaction proceeds by a protonation-deprotonation sequence. 1985, American Chemical Society. All rights reserved.

published proceedings

  • JOURNAL OF ORGANIC CHEMISTRY

author list (cited authors)

  • SMITH, J. K., BERGBREITER, D. E., & NEWCOMB, M.

citation count

  • 16

complete list of authors

  • SMITH, JK||BERGBREITER, DE||NEWCOMB, M

publication date

  • November 1985