Abstract
Abstract Ghloromethyl methyl sulfoxide undergoes a Darzens-type reaction with carbonyl compounds in the presence of potassium t-butoxide in t-butanol to afford methylsulfinyloxirane derivatives. The stereochemistry of this reaction has been studied. The reaction with a symmetrical ketone appeared to proceed stereospecifically to give only one isomer. On the other hand, the reaction with unsymmetrical ketones such as pinacolone or acetophenone produced a mixture of two diastereoisomers, in which a thermodynamically unstable isomer was predominant. The reaction with thiobenzophenone gave 1,1-diphenyl-2-methylsulfinylethylene which seems to have been formed from the intermediacy of 2,2-diphenyl-3-methylsulfinylthiirane. Mechanisms of these reactions are also discussed.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
