Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

Submitting author affiliation:
Kindai University, Osaka, Japan

Beilstein Arch. 2021, 202138.

Published 21 May 2021

cc-by Logo
This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


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

Supporting Information

Format: PDF Size: 418.0 KB   Download
Format: CIF Size: 267.4 KB   Download

How to Cite

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 Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.