Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system
Abstract
Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure. © 2001 Elsevier Science Ltd.
Publication Title
Tetrahedron Letters
Recommended Citation
Thomas, A., Monk, K., Abraham, S., Lee, S., & Garner, C. (2001). Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system. Tetrahedron Letters, 42 (12), 2261-2263. https://doi.org/10.1016/S0040-4039(01)00089-2
