Regio- and stereoselective rearrangements of formyl [2.2.1]bicyclic carbinols in methanol

Individual treatments of camphor- and camphene-derived formyl [2.2.1]bicyclic carbinols with blank methanol, methanol containing acidic acid, and methanol containing sodium methoxide provided corresponding [3.2.1]bicyclic hydroxy ketones. Rearrangement of each bicyclic carbinol was found to be regio...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2009-11, Vol.65 (47), p.9854-9861
Main Authors: Yang, Te-Fang, Tseng, Chih-Hao, Shen, Chien-Hung, Chen, Li-Hsun, Kao, Li-Ta
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Bicyclic dimer
Bicyclic hydroxy ketones
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Ring expansion
Selective rearrangement
Terpenoids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Individual treatments of camphor- and camphene-derived formyl [2.2.1]bicyclic carbinols with blank methanol, methanol containing acidic acid, and methanol containing sodium methoxide provided corresponding [3.2.1]bicyclic hydroxy ketones. Rearrangement of each bicyclic carbinol was found to be regio- and stereoselective under neutral and acidic conditions. Mechanisms of these rearrangements were discussed. Both camphor- and camphene-derived formyl bicyclic carbinols could rearrange in methanol and give the corresponding [3.2.1]bicyclic hydroxy ketones. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.09.057