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Updated: Jun 24, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Trialkylamines more planar at nitrogen than triisopropylamine in the solid state
Minmin Yang1, Thomas Albrecht-Schmitt, Vince Cammarata
1Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849-5312, USA.
Researchers synthesized sterically hindered amines using rhodium carbenoid insertion. These amines exhibit nearly planar nitrogen atoms, challenging previous assumptions about triisopropylamine
Area of Science:
- Organic Chemistry
- Stereochemistry
- Crystallography
Background:
- Sterically hindered amines are important in synthesis.
- The nitrogen atom in trialkylamines is typically pyramidal.
- Triisopropylamine was previously considered perfectly planar.
Purpose of the Study:
- To synthesize sterically hindered amines.
- To investigate the geometry of nitrogen atoms in these amines.
- To understand factors influencing nitrogen planarity.
Main Methods:
- Rhodium carbenoid insertion into N-H bonds.
- X-ray crystallography for structural analysis.
- Cyclic voltammetry for electronic properties.
Main Results:
- Efficient synthesis of congested amines like 2-(diisopropylamino)propane-1,3-diol and 2-(2,2,6,6-tetramethyl-1-piperidinyl)propane-1,3-diol.
- X-ray crystallography revealed nearly planar nitrogen atoms, more so than in triisopropylamine.
- Proposed an orbital interaction model to explain nitrogen planarity with the 1,3-dihydroxy-2-propyl group.
Conclusions:
- Sterically hindered amines can be synthesized with near-planar nitrogen centers.
- The degree of nitrogen planarity in these amines is quantifiable and can exceed that of triisopropylamine.
- No direct correlation was found between nitrogen planarity and oxidation potential.
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