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Updated: Jul 12, 2025
Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
o-Hydroxyarylphosphanes: Strategies for Syntheses of Configurationally Stable, Electronically and Sterically Tunable
1Emeritus Inorganic Chemistry, Institute of Biochemistry, University Greifswald, 17487, Greifswald, Germany.
Abstract:
o-Hydroxyarylphosphanes are fascinating compounds by their multiple-reactivity features, attributed to the ambident hard and soft Lewis- and also Brønstedt acid-base properties, wide tuning opportunities via backbone substituents with ±mesomeric and inductive, at P and in o-position to P and O also steric effects, and in addition, the configurational stability at three-valent phosphorus. Air sensitivity may be overcome by reversible protection with BH3 , but the easy oxidation to P(V)-compounds may also be used. Since the first reports on the title compounds ca. 50 years ago the multiple reactivity has led to versatile applications. This includes various P-E-O and P=C-O heterocycles, a multitude of O-substituted derivatives including acyl derivatives for traceless Staudinger couplings of biomolecules with labels or functional substituents, phosphane-phosphite ligands, which like the o-phosphanylphenols itself form a range of transition metal complexes and catalysts. Also main group metal complexes and (bi)arylphosphonium-organocatalysts are derived. Within this review the various strategies for the access of the starting materials are illuminated, including few hints to selected applications.
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