93021-76-2

Upstream product

• 2674-04-6 diphenyl cadmium 
• 6261-32-1 (E)-2-benzylidene-1-tetralone 
• 14209-41-7 3H-indene-1-carboxylic acid 
• 6282-87-7 3-(2-chlorophenyl)-propanol 
• 90347-04-9 1-chloro-2-(3-chloro-propyl)-benzene 
• 30573-88-7 ethyl 3-(2-chlorophenyl)propanoate 
• 91552-19-1 4-(2-chloro-phenyl)-butyronitrile 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 
• 19156-10-6 indan-1-carbonyl chloride 
• 92907-13-6 4-(2-Chlor-phenyl)-1-oxo-1-phenyl-butan 
• 14381-42-1 Indan-1-carboxylic acid 

Downstream Products

• 13245-90-4 1-benzhydrylidene-indene 
• 95625-57-3 1-(α-Oxy-benzhydryl)-hydrinden 

Relevant academic research and scientific papers

Biomimetic reactions in organic synthesis: Semi-pinacol rearrangements of some spirocyclic epoxyalcohols derived from Julia-Colonna asymmetric epoxidations

Epoxy tert-alcohols have been prepared from (E)-enones in a two-step approach consisting of Julia-Colonna asymmetric epoxidation followed by Grignard alkylation of the epoxyketone. On treatment with sub-stoichiometric amounts of Yb(OTf)3 these trans-epoxyalcohols underwent efficient stereoselective semi-pinacol rearrangement to afford anti-α-phenyl-β-hydroxy-ketones (aldols). Under the same conditions, spirocyclic epoxyalcohols derived from 1-tetralone and 1-benzosuberone undergo either ring contraction (via semi-pinacol rearrangement) or fragmentation. A mechanistic rationale is presented to explain the formation of the various products.

Et2Zn-mediated rearrangement of bromohydrins

(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.