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

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.

authors

• Bergbreiter, David

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

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Organic Chemistry  Journal

Digital Object Identifier (DOI)

• 10.1021/jo00328a044

start page

• 3157

end page

• 3158

volume

• 46

issue

• 15

URL

• http://dx.doi.org/10.1021/jo00328a044