In Section 14.11, we learned that 1 is a strong methyl transfer agent. However, when
Chapter 14, Problem 14.65(choose chapter or problem)
In Section 14.11, we learned that 1 is a strong methyl transfer agent. However, when treated with a strong base (e.g., NaH), 1 is converted into a special type of carbanion, called a sulfur ylide, which can function as a methylene (CH2) transfer agent. Specifically, treating the sulfur ylide with a ketone affords an epoxide, with dimethyl sulfide (DMS) being generated as a by-product (Synth. Commun. 2003, 33, 21352143). Propose a plausible mechanism for this process, known as the Corey-Chaykovsky reaction. S CH3 H3C H3C 1) NaH Ph CH3 O + S H3C H3C 1 O CH3 2) Ph
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