Rapid Preparation of Cycloheptane Ring from 1,2-Diketone and Bis(iodozincio)methane via Oxy-Cope Rearrangement Using Microflow System

Treatment of 1,6-dialkylhexa-1,5-diene-3,4-diones with bis(iodozincio)methane at −78 °C for several hours gave cis-dialkenylcyclopropane-1,2-diols which rearranged into the zinc alkoxides of cis-5,6-dialkylcyclohepta-3,7-diene-1,3-diol in good yields at room temperature as a one-pot reaction. The re...

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Bibliographic Details
Published in:Chemistry letters 2012-06, Vol.41 (6), p.628-629
Main Authors: Haraguchi, Ryosuke, Takada, Yoshiaki, Matsubara, Seijiro
Format: Article
Language:English
Subjects:
Alkoxides
Temperature control
Zinc
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Summary:Treatment of 1,6-dialkylhexa-1,5-diene-3,4-diones with bis(iodozincio)methane at −78 °C for several hours gave cis-dialkenylcyclopropane-1,2-diols which rearranged into the zinc alkoxides of cis-5,6-dialkylcyclohepta-3,7-diene-1,3-diol in good yields at room temperature as a one-pot reaction. The reaction should be performed under the careful temperature control. When the reaction was performed using a microflow system, these two-step reactions were able to be performed in a few seconds at room temperature.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2012.628