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An epoxide is formed when an aldehyde or ketone is treated with a sulfonium ylid. An example of this transformation is shown below. CH3 CH3 DMSO (solvent) CH3 CH3 Wo did nat din

An epoxide is formed when an aldehyde or ketone is treated with a sulfonium ylid. An example of this transformation is shown below. CH3 CH3 DMSO (solvent) CH3 CH3 Wo did nat din

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Propose a curved-arrow mechanism for this reaction. Use curved arrows to show movement of electron pairs, and draw structures for all important reaction intermediates. Be sure to show all lone pairs and nonzero formal charges.
### Epoxide Formation via Sulfonium Ylid Treatment When an aldehyde or ketone is treated with a sulfonium ylid, it forms an epoxide. This transformation is an essential reaction in organic chemistry. #### Reaction Example - **Reactants:** - Cyclohexanone (a cyclic ketone) with an oxygen double bond. - Sulfonium ylid: \((CH_3)_2S^+CH_2^-\) - **Reagents and Conditions:** - Solvent: Dimethyl sulfoxide (DMSO). - **Products:** - Epoxide: A three-membered cyclic ether with an oxygen atom. - Byproduct: \((CH_3)_2S\) The process involves the transfer of the ylides methylene group to the carbonyl carbon of the ketone, resulting in the epoxide formation and the release of dimethyl sulfide. This transformation showcases the ability of ylides to engage in effective nucleophilic attacks, facilitating the creation of strained three-membered rings which are valuable intermediates in synthesis.
Transcribed Image Text:### Epoxide Formation via Sulfonium Ylid Treatment When an aldehyde or ketone is treated with a sulfonium ylid, it forms an epoxide. This transformation is an essential reaction in organic chemistry. #### Reaction Example - **Reactants:** - Cyclohexanone (a cyclic ketone) with an oxygen double bond. - Sulfonium ylid: \((CH_3)_2S^+CH_2^-\) - **Reagents and Conditions:** - Solvent: Dimethyl sulfoxide (DMSO). - **Products:** - Epoxide: A three-membered cyclic ether with an oxygen atom. - Byproduct: \((CH_3)_2S\) The process involves the transfer of the ylides methylene group to the carbonyl carbon of the ketone, resulting in the epoxide formation and the release of dimethyl sulfide. This transformation showcases the ability of ylides to engage in effective nucleophilic attacks, facilitating the creation of strained three-membered rings which are valuable intermediates in synthesis.
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