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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
S-alkylation of soft scorpionates
Rajeev Rajasekharan-Nair1, Dean Moore, Kirsten Chalmers
1WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 9, 2013
Summary
Soft scorpionate alkylation reactions were studied, revealing kinetic factors drive outcomes. Weak B-N bonds in these boron-based ligands limit their advanced chemistry applications.
Area of Science:
- Organometallic Chemistry
- Boron Chemistry
- Coordination Chemistry
Background:
- Soft scorpionates are versatile ligands in coordination chemistry.
- Understanding their reactivity is crucial for developing new synthetic methodologies.
Purpose of the Study:
- To investigate the alkylation reactions of soft scorpionates.
- To characterize the resulting products and elucidate reaction mechanisms.
- To assess the stability and limitations of soft scorpionates in chemical synthesis.
Main Methods:
- Synthesis and structural characterization of hydrotris(S-alkyl-methimazolyl)borate dications.
- Density Functional Theory (DFT) analysis of alkylation pathways.
- Investigation of reactions with alternative imine thiones.
Main Results:
- Successful isolation and characterization of specific alkylated scorpionate dications.
- DFT analysis indicated kinetic control in C=S versus B-H alkylation.
- Reactions with alternative imine thiones led to decomposition and simple S-alkylated heterocycles.
- Structural characterization of a novel sodium-containing borate complex.
Conclusions:
- Alkylation of soft scorpionates is influenced by kinetic factors.
- The B-N bond in soft scorpionates exhibits inherent weakness.
- This instability has implications for their utility in advanced chemical applications.
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