Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols?
Organic & Biomolecular Chemistry Pub Date: 2015-03-18 DOI: 10.1039/C5OB00305A
Abstract
In refluxing 9?:?1 (v/v) H2O–1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which are difficult to synthesize by other means.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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