α-chloro ketoximes as precursors of nitrosoalkenes: Preparation, stereochemistry and conformation

Scott E Denmark, Michael S. Dappen

Research output: Contribution to journalArticlepeer-review

Abstract

The ability of-chloro and α, β-epoxy ketoximes and silyloximes of substituted cyclohexanones to serve as precursors for nitrosoalkenes has been investigated. α-Chloro ketoximes produced nitrosoalkenes efficiently with triethylamine regardless of oxime geometry or disposition of the chlorine atom. α-Chloro silyloximes were less efficientin production of nitrosoalkenes with tetrabutylammonium fluoride and led to a faster decay of reactive species. Nitrosoalkenes that cannot tautomerize are extremely stable and efficiently generated even from silyloximes. α,β-Epoxy ketoximes were shown to be incapable of generating nitrosoalkenes in detectable amounts under several conditions. A striking dependence of oxime geometry on oximation conditions was discovered. (tert-Butyldimethyl) silyloxime (E)-trans-12 showed an unusual preference for the conformation in which bothsubstituents assume axial orientations.

Original languageEnglish (US)
Pages (from-to)798-806
Number of pages9
JournalJournal of Organic Chemistry
Volume49
Issue number5
DOIs
StatePublished - Dec 1984

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'α-chloro ketoximes as precursors of nitrosoalkenes: Preparation, stereochemistry and conformation'. Together they form a unique fingerprint.

Cite this