amarium Diiodide-Mediated Reductive Intramolecular Cyclization in Spirane Synthesis

碩士 === 國立中正大學 === 化學所 === 98 === This thesis describes a methodology designed to access spiro compounds in a rapid and efficient manner. Treatment of β-methoxycycloalkenones 68 with Grignard reagent which were prepared from bromides 70 and magnesinm, follow by acidic aqueous workup provided enone-al...

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Bibliographic Details
Main Authors: Chi-Wei Hsu, 許奇瑋
Other Authors: Day-Shin Hsu
Format: Others
Language:zh-TW
Published: 2010
Online Access:http://ndltd.ncl.edu.tw/handle/44264074441517770644
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Summary:碩士 === 國立中正大學 === 化學所 === 98 === This thesis describes a methodology designed to access spiro compounds in a rapid and efficient manner. Treatment of β-methoxycycloalkenones 68 with Grignard reagent which were prepared from bromides 70 and magnesinm, follow by acidic aqueous workup provided enone-aldehyedes 61. Enone-aldehyedes were then subjected to samarium diiodide under mild conditions and obtained various apirocyclic hydrocarbons 67 in good yields. Oxidation of hydroxyketone 67 with PCC afforded spirodiketone 62.