The Stereochemistry of Chloro-bis(N-morpholino)phenylsilane

Gerald Huber, Annette Schier, Hubert Schmidbaur

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Treatment of phenyltrichlorosilane with an excess of morpholine and N-lithium-morpholide in pentane/toluene affords only the disubstitution product Cl(Ph)Si(Mor)2 with Mor = O(CH2CH2)2N-. The third halogen atom is not replaced owing to sterical hindrance. The title compound crystallizes with two independent molecules in the unit cell. These two molecules can be classified as enantiomers, because a disrotatory twist of the two morpholino ligands away from the potential mirror plane induces a chiral conformation. In benzene solution there is racemization owing to completely free rotation, chair/boat interconversion, and nitrogen inversion of the morpholino groups on the NMR time scale, but all CH2 protons remain anisochronous (diastereotopic).

Original languageEnglish
Pages (from-to)18-20
Number of pages3
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume54
Issue number1
DOIs
StatePublished - Jan 1999
Externally publishedYes

Keywords

  • Aminosilanes
  • Crystal structure
  • NMR data
  • Silylamines
  • Symmetry

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