REGIOSELECTIVITY IN DEPROTONATION OF IMINES DERIVED FROM 3-PENTANONE Academic Article uri icon

abstract

  • Regioselectivity in deprotonation of (Z)-tertbutyl, (Z)-cyclohexyl, (Z)-benzyl, and (Z)-phenyl ketimines of 3-pentanone has been shown to be generally low and variable. Deprotonation of 13CH3-labeled Z ketimines with either lithium diisopropylamide or lithium diethylamide in THF and methylation at -78 C was used to determine regiochemistry. Syn/anti deprotonation ratios varied from 74/26 to 22/78 with different ketimines and different bases. 1981, 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

  • 10

complete list of authors

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

publication date

  • July 1981