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8-Oxabicyclo[5.1.0]octa-2,4-dien Thermische und lichtinduzierte Isomerisierung

✍ Scribed by Peter Schiess; Markus Wisson

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
771 KB
Volume
57
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

8‐Oxabicyclo[5.1.0]octa‐2, 4‐diene (1) yields 2,4,6‐heptatrienaldehyde as major primary rearrangement product upon pyrolysis in a flow system between 200 and 300°. Above 500° o‐cresol, benzaldehyde and benzene are obtained. Bicyclo[3.2.0]hept‐2‐en‐7‐one, 2,3‐ and 2, 5‐dihydrobenzaldehyde are shown to be intermediates in this transformation to stable aromatic products. The observed conversions can be rationalized as proceeding mostly through allowed pericyclic reaction steps with heterogeneous, acid catalysed reactions participating to a minor extent. Irradiation of 1 affords 3‐oxatricyclo[4.2.0.0^2,4^]oct‐7‐ene, 2,4,6‐heptatrienal and 3,5‐cycloheptadienone. Upon sensitized irradiation only the latter two compounds are formed.

📜 SIMILAR VOLUMES

8-Oxabicyclo[5.1.0]octa-2,4-dien, redukt
8-Oxabicyclo[5.1.0]octa-2,4-dien, reduktive und säurekatalysierte Ringöffnung
✍ Peter Schiess; Markus Wisson 📂 Article 📅 1974 🏛 John Wiley and Sons 🌐 German ⚖ 503 KB

## Abstract 8‐Oxabicyclo[5.1.0]octa‐2,4‐diene (**1**) is obtained from cycloheptatriene with commercial 40% peracetic acid. Upon catalytic and LiAlH~4~ reduction the allylic CO‐bond in **1** is cleaved. Acid catalised hydrolysis leads to a mixture of all six possible isomeric cycloheptadienediols.

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4,8-Dioxabicyclo[5.1.0]octa-2,5-diene
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