Different Pathways in the Base-Promoted Isomerization of Benzyl Oxiranyl Ethers |
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| Authors: | Mordini Alessandro Bindi Simona Pecchi Sabina Degl'Innocenti Alessandro Reginato Gianna Serci Alessandro |
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| Institution: | Centro CNR Composti Eterociclici, c/o Dipartimento di Chimica Organica "U. Schiff", via G. Capponi 9, 50121 Firenze, Italy. |
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| Abstract: | The base-promoted isomerization of benzyl oxiranyl ethers was investigated. In particular it was shown that the reaction may proceed toward two main regioisomeric products: a benzyl vinyl ether or a 2-aryl-3-(hydroxyalkyl)oxetane, depending on subtle variations in the substitution on the phenyl ring. Disubstituted oxetanes were obtained in a stereoselective manner, thus providing a good entry to this class of synthetically useful compounds. |
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