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Chapter 16: Problem 27

It is possible to generate sulfur ylides in a manner similar to that used to produce phosphonium ylides. For example, treating a sulfonium salt with a strong base gives the sulfur ylide.

Short Answer

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Short Answer: To generate a sulfur ylide from a sulfonium salt, simply treat the sulfonium salt with a strong base. The base will remove an acidic proton from an organic group attached to the sulfur atom, while the sulfur atom obtains a lone pair of electrons, forming the sulfur ylide.

Step by step solution

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1. Understanding Sulfonium Salt, Sulfur Ylide, and Phosphonium Ylide

Before we dive into the process of generating sulfur ylides, let's first understand what sulfonium salt, sulfur ylide, and phosphonium ylide are. A sulfonium salt is a compound containing a positively charged sulfur atom with three organic groups attached to it and a negatively charged counter ion (e.g., chloride, bromide). A sulfur ylide, on the other hand, is a neutral compound containing a divalent sulfur atom (elemental state), which is bonded to two organic groups and a heteroatom (such as nitrogen or oxygen) with a lone pair of electrons, making it nucleophilic and reactive. Phosphonium ylides are similar to sulfur ylides but contain a positively charged phosphorus atom instead of sulfur.
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2. Treating Sulfonium Salt with a Strong Base

To generate a sulfur ylide from a sulfonium salt, we use a strong base. The base abstracts the acidic proton (H) from the organic group attached to the sulfur atom in the sulfonium salt. The electrons from the S-H bond move to the sulfur atom, creating a nucleophilic sulfur ylide with a lone pair on the sulfur atom. This process is depicted as follows: Sulfonium Salt + Strong Base -> Sulfur Ylide
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3. Example of Generating Sulfur Ylide

Here is an example of generating a sulfur ylide from a sulfonium salt: 1. Starting with a sulfonium salt: (CH3)_3S^+ Cl^- 2. Treating the sulfonium salt with a strong base, such as NaOH: (CH3)_3S^+ Cl^- + NaOH -> (CH3)_2SCH2^- + NaCl + H2O 3. The final product is the sulfur ylide: (CH3)_2SCH2^- In summary, to generate a sulfur ylide from a sulfonium salt, treat the sulfonium salt with a strong base. The base will abstract the acidic proton from the organic group attached to the sulfur atom, and the sulfur atom will gain a lone pair of electrons, forming the sulfur ylide.

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