Abstract
The orientation of the addition of benzenesulphenyl chlorides to phenylacetylene in ethyl acetate is largely shifted from anti-Markownikoff to Markownikoff by strong acids like trifluoroacetic and hydrochloric. No effect was observed on the addition to but-1-yne. The results fit the scheme proposed to explain the effect of solvent on the orientation, and confirm that production of the Markownikoff orientation is related to the possibility of forming a highly polar structure from an initial adduct between the sulphenyl chloride and the aceylene derivative, which would otherwise yield the anti-Markownikoff adduct by internal collapse. A further proof of the trans-stereochemistry of the additions is given.
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.
