title: Zn(II)- or Rh(I)-catalyzed rearrangement of silylated [1,1'-bi(cyclopropan)]-2'-en-1-ols.
abstract: The rearrangement reactions of silylated alcohols bearing the highly strained structures of cyclopropene and cyclopropanol connected in adjacent positions have been studied under ZnI2- and Rh(I)-catalyzed conditions. The results show intriguing carbon skeletal reorganizations of such system under these conditions. The ZnI2-catalyzed reaction proceeds with C-O cleavage and the rearrangement of the resultant carbon cation, leading to the breaking of the C-C single bond that connects two three-memebered rings. In contrast, the Rh(I)-catalyzed reaction involves σ-bond oxidative addition of the cyclopropene moiety, followed by β-carbon elimination of the cyclopropane moiety.
authors.affiliation: Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Hang
authors.initials: H
authors.lastname: Zhang
authors.forename: Changkun
authors.initials: C
authors.lastname: Li
authors.forename: Guojun
authors.initials: G
authors.lastname: Xie
authors.forename: Bo
authors.initials: B
authors.lastname: Wang
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jianbo
authors.initials: J
authors.lastname: Wang
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D000438:Alcohols; D003521:Cyclopropanes; D012821:Silanes; C030797:cyclopropane; D012238:Rhodium; D015032:Zinc