81707-21-3Relevant academic research and scientific papers
Et2Zn-mediated rearrangement of bromohydrins
Li, Lezhen,Cai, Peijie,Guo, Qingxiang,Xue, Song
, p. 3516 - 3522 (2008/09/20)
(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.
Reaction of 1-Substituted Indenes with Diborane or N-Bromoacetamide in Protic Solvents. The Effect of the Substituent on the Stereochemistry of Addition
Miura, Masahiro,Yoshida, Masaya,Nojima, Masatomo,Kusabayashi, Shigekazu
, p. 79 - 84 (2007/10/02)
The reaction of 1-substituted indenes with diborane or N-bromoacetamide (NBA) in protic solvents has been investigated to determine the effect of an increase of steric bulk of the substituent on the stereochemical course of addition.In the hydroboration reaction the proportion of the products via attack by diborane from the less hindered side increases, as the steric bulk of the substituent at C-1 increases.The reaction with NBA in aqueous dioxan, followed by acetylation, gave a mixture of 3-substituted-1-acetoxy-2-bromoindans with trans, trans and trans,cis-configuration: 1-phenylindene gave mainly trans, trans-1-acetoxy-2-bromo-3-phenylindan, while trans,cis-1-acetoxy-2-bromo-3-methylindan was the maior product in the case of 1-methylindene.
