Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcoholsElectronic supplementary information (ESI) available: All 1H and 13C NMR spectra. CCDC 1008768. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob00305a

In refluxing 9 : 1 (v/v) H 2 O-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 tricycli...

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Main Authors: Li, Pei-Fang, Yi, Cheng-Bo, Qu, Jin
Format: Article
Language:English
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Summary:In refluxing 9 : 1 (v/v) H 2 O-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. Hot water can promote the rearrangements of various types of cyclopropyl carbinols to afford acyclic or cyclic homoallylic alcohols in high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00305a