Abstract
1. A method which fully eliminates the competing free-radical reaction was developed for the nucleophilic addition of thiols to alkylacetylenes. 2. Under purely nucleophilic conditions steric effects substantially affect the regioorieatatioa of a thiolate ion adding to tert-butylacetylene. The proportion of attack at theβ atom, of the C ≡ C bond increases with increase in the volume of the nucleophilic reagent. 3. Theβ adducts are formed strictly stereospecifically by a nucleophilic mechanism, of 1,2-anti-addition, and steric effects do not affect the stereochemistry of the process. 4. It was found that the ratio of the regioisomers formed in the reaction of 1-alkynes with thiols and alcohols correlates well with Charton' s steric constants for alkyl groups in the nucleophilic reagent.
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 callMore From: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Disclaimer: 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.
