Allylic oxidation of myrcene

Bu çalışmada, açık zincirli monoterpen olan mirsenin allilik yükseltgenme reaksiyonları incelenmiştir. Burada amaçlanan, çam kabuk böceği feromonu olan , mirsenin ipsdienole dönüştürülmesidir. Bu çalışmada yükseltgen olarak kromtrioksit (Cr03), kromtrioksit-piridin kompleksi, piridinyum klorokromat (PCC), tersiyer butil hidroperoksit (t-BuOOH) ve tersiyer butil perbenzoat (TBPB), solvent olarak benzotriflorür (BTF), diklorometan, asetonitril, CCl4,asetanhidrit, benzen, asetik asit, etil asetat ve glasiyel asetik asit, katalizör olarak ise bazı Cu(l) ve Cu(ll) tuzları, bakır tuzları ile birlikte L-prolin, S-prolin kompleksleri, SeO2 ve PdCl2 kullanılmıştır. Sözü edilen katalizörler ve yükseltgenler ile farklı, yöntemler uygulanmış ve reaksiyon sonucunda oluşan ürünler GC-MS ile belirlenmiştir. Mirsenin ipsdienole dönüştürülmesinde yeterince başarı sağlanamamıştır; çünkü,mirsenin allilik yükseltgenmeye uğramadan önce bazı halkalı ve açık zincirli bileşiklere izomerleştiği gözlenmiştir. Mirsenin allilik yükseltgenmesinde en iyi verimler, yükseltgen olarak piridinyum klorokromatın kullanılmasıyla elde edilmiştir. Ayrıca çözücü olarak benzotriflorür (BTF)'ün kullanılması yükseltgenme ürünleri veriminin daha da artmasını sağlamıştır. Özellikle, mirsenin ipsdienole dönüştürülmesi ancak bu çözücünün kullanılması ile gerçekleştirilebilmiştir.

Mirsen'in allilik oksidasyonu

In this study, allylic oxidation reaction of open chain monoterpene, myrcene was studied. Our aim was to obtain pine-bark insect pheromones ipsdienol from myrcene. In the experiments, chromium trioxide (CrO3), CrO3-pyridine complex, pyridinium chlorochromate (PCC), tert-buthyl hydroperoxide (t-BuOOH) and tert-buthyl perbenzoate (TBPB) were chosen as oxidants, benzotrifluoride, dichloromethane, , acetonitrile, CCl4, acetanhydride, benzene, acetic acid, ethylacetate ve glacial acetic acid as solvents, while some salts of Cu(l) and Cu(ll) compounds and together with L-prolin, S-prolin, SeO2 and PdCl2 were used as catalysts. Reaction products were determined by GC-MS analysis.The conversion of myrcene to ipsdienol was not so successful. Because, myrcene tends to isomerisation to different cyclic and open chain compounds before its allylic oxidation could occur. In the allylic oxidation reaction of particularly, the conversion of myrcene to ipsdienol could have been obtained with BTF only.

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