Orientation in Base-Promoted Dehydrohalogenation of N-(Chlorobenzyl)-n-butylamine

Richard A. Bartsch, Bong Rae Cho

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Although the mechanisms of olefin formation by basepromoted dehydrohalogenation have been extensively investigated,3, 4 the removal of hydrogen halide across C-N bonds has received little attention. The only kinetic studies of imine-forming dehydrohalogenation involve the reactions of alkyldifluoroamines, RCH2NF2, in water-diglyme at 25-75 °C reported by Braumann and Hill.5, 6 In contrast to the strongly basic conditions required for alkene formation by dehydrofluorination of closely related 1, 1-difluoro-2-arylethanes,7 water was a sufficiently strong base to induce eliminations from the alkyldifluoroamines. These observations underscore the marked facility of carbon-heteroatom multiple bond forming eliminations when compared with analogous processes leading to alkenes or alkynes.

Original languageEnglish
Pages (from-to)145-146
Number of pages2
JournalJournal of Organic Chemistry
Volume44
Issue number1
DOIs
Publication statusPublished - 1979 Feb 1

ASJC Scopus subject areas

  • Organic Chemistry

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