The reactions of aldehydes and a non-conjugated alcohol, (E)-octa-3,7-dien-1-ol, in the presence of halogen-containing reagents afforded the corresponding halogenated bicyclic molecules in good yields. The optimization, scope and limitations of the reactions as well as scale-up reactions have been examined. Quantum chemical calculations helped clarify the microscopic mechanism of a key reaction process, the introduction of a Cl atom to a bicyclic carbocation.
Keywords: Prins Cyclization; C－C Bond Formation; Bicyclic Molecules; Sequential Reactions
When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Matsumoto, K.; Ohtsuka, K.; Hasebe, N.; Terada, K.; Maekawa, M.; Nakao, Y.; Nishiwaki, K.; Ando, H. Beilstein Arch. 2021, 202138. doi:10.3762/bxiv.2021.38.v1
|Download RIS (Reference Manager)||Download BIB (BIBTEX)|