Abstract

In the presence of potassium hexamethyldisilazide and 18-crown-6 in THF at room temperature, 2-benzyloxycyclo-octanone and its Δ 5 -unsaturated congener undergo a two-stage rearrangement to give symmetrical seven-membered ring products. The pathway consists of the sequential operation of an O → C 1,2-shift and an u-ketol rearrangement. The greater thermodynamic stability of the cycloheptane or cycloheptene generated in this fashion is substantiated by MM3 calculations.

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 call

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.