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Issue 17, 2015
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Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

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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.

Graphical abstract: Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

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Publication details

The article was received on 12 Feb 2015, accepted on 18 Mar 2015 and first published on 18 Mar 2015


Article type: Paper
DOI: 10.1039/C5OB00305A
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Org. Biomol. Chem., 2015,13, 5012-5021

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    Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

    P. Li, C. Yi and J. Qu, Org. Biomol. Chem., 2015, 13, 5012
    DOI: 10.1039/C5OB00305A

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