ChemInform Abstract: Onio-Assisted SN2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives.
✍ Scribed by R. WEISS; M. HANDKE; S. REICHEL; F. HAMPEL
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 42 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Onio-Assisted S N 2-Reactions: General Access to Symmetrical and Unsymmetrical Geminally Bisonio Substituted Methane Derivatives.
-A wide range of the title compounds are synthesized from the arsonium salt (I) containing a 1,1-biselectrophilic Csp3 center. With equimolar amounts of neutral nucleophiles, selective substitution of the triflate group takes place under mild conditions. The arsonio function in these products can undergo subsequent S N -reaction with a second nucleophile yielding a series of novel unsymmetrical 1,1-bisonium salts such as (IV). Both nucleofuges in salt (I) can also be substituted in one step to give the corresponding symmetrical salts like (XIII) and (XIV). The experimental results are rationalized on the basis of a simple MO model. -(