Abstract
Determination of the reactivity of Bu 3Sn· with the carbonyl group of an alkyl aryl ketone and the chlorine atom of a primary alkyl chloride have shown similar types of reaction. These results led us to reconsider the mechanism of 2-phenyltetrahydrofuran formation in reduction reactions of γ-chlorobutyrophenone by tributyltin hydride. This cyclic ether was obtained by elimination of tributyltin chloride from the product of carbonyl hydrostannation. A similar study on an aldehyde and 1-chloroalkane revealed the mechanism of cyclohexanol formation in reduction reactions of 6-chlorohexanal by tributyltin hydride. Tributyltin hydride treatment of 7-chloroheptan-2-one and 6-chlorohexan-2-one led to heptan-2-one and hexan-2-one in good yields; no cyclization product is observed.
Published Version
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.
