title: Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols.
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.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, China. qujin@nankai.edu.cn.
authors.forename: Pei-Fang
authors.initials: PF
authors.lastname: Li
authors.forename: Cheng-Bo
authors.initials: CB
authors.lastname: Yi
authors.forename: Jin
authors.initials: J
authors.lastname: Qu
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D020005:Propanols; D014867:Water; C006463:allyl alcohol; D000432:Methanol