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Interconversion of cis- and trans-Fused Oxabicyclo[5.2.0]nonan-2-ones

✍ Scribed by Kerstin Schmidt; Paul Margaretha

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
199 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

On irradiation (350 nm) in the presence of alkenes (2,3‐dimethylbut‐2‐ene, 1,1‐dimethoxyethene, and 2,4,4‐trimethylpent‐1‐ene), benzoxepinone 1 and dioxepinone 2 are converted into mixtures of cis‐ and trans‐fused oxabicyclo[5.2.0]nonan‐2‐ones. Their relative thermodynamic stabilities (as reflected by the observed diastereoisomer ratios after equilibration with basic alumina) depend on the substitution pattern of the alkene moiety.

📜 SIMILAR VOLUMES

Synthesis of trans-Fused Oxabicyclo[5.2.
Synthesis of trans-Fused Oxabicyclo[5.2.0]nonan-2-ones via [2+2] Photocycloaddition of Oxepinones to Conjugated Alkenes
✍ Kerstin Schmidt; Paul Margaretha 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 German ⚖ 150 KB

## Abstract On irradiation (350 nm) in the presence of 2,3‐dimethylbuta‐1,3‐diene, benzoxepinone **2** and dioxepinone **3** were converted regio‐ and diastereoselectively to __trans__‐fused oxabicyclo[5.2.0]nonanones **5** and **9**, respectively.

Ring-transformation reactions of 5-hydro
Ring-transformation reactions of 5-hydroxy-2-oxabicyclo[3.2.0]-heptan-4-ones and 5-hydroxy-2-oxabicyclo[3.2.0]hept-6-en-4-ones
✍ Tetsuro Shimo; Hidemi Minamishin; Kenichi Somekawa 📂 Article 📅 1997 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 196 KB

## Abstract Dehydrochlorination of chlorinated 5‐hydroxy‐2‐oxabicyclo[3.2.0]heptan‐4‐ones, 3a‐c, which were obtained from the photo[2+2]cycloadditions between 4‐hydroxy‐3(2__H__)‐furanone 1 and chloroethylenes, with triethylamine gave 2‐ethenyl‐3(2__H__)‐furanones 4a,b or 2‐(2‐cyanoethyl)‐3(2__H__)

cis-8-Aza­bi­cyclo­[5.2.0]­nonan-9-one
cis-8-Aza­bi­cyclo­[5.2.0]­nonan-9-one
✍ Argay, Gyula ;Kálmán, Alajos ;Bernáth, Gábor ;Gyarmati, Zsuzsanna Cs. 📂 Article 📅 2004 🏛 International Union of Crystallography 🌐 English ⚖ 192 KB

Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.005 A Ê R factor = 0.066 wR factor = 0.227 Data-to-parameter ratio = 10.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.