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[3.3.1]-propellane-2,8-dione

✍ Scribed by I. David Reingold; James Drake

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
126 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title compound was prepared by transammlar addition of a carbene to an exocyclic double bond. Rhodium acetate catalyzed decomposition of 2-diazo-&methylene-1,3-cyclooctanedione gave 1 quantitatively.

We wish to report the first synthesis of the title compound, 1, and a new approach to propellanes which we believe will have broad applications to other systems as well. We were intrigued by the idea of approaching this system from a monocyclic precursor using a transannular ring closure, as shown in Scheme 1. The necessary precursor, 6methylenecyclooctane-1,3-dione

(3), should in principle be readily available by acyloin condensation followed by ring expansion of the appropriate diester, a method Pirmng has used with great success to make the parent cyclooctanedione.2

We are pleased to report that this approach has worked exactly as planned.

📜 SIMILAR VOLUMES

Propellanes. Part LXX. The oximes of [4.
Propellanes. Part LXX. The oximes of [4.3.3]propellane-8,11-dione
✍ Soundararajan Bhanumati; Pnina Ashkenazi; David Ginsburg 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 72 KB 👁 1 views

## Abstract The mono‐oxime and dioxime of the title compound have been prepared.

Propellanes. Part LXXX. Baeyer-Villiger
Propellanes. Part LXXX. Baeyer-Villiger Oxidation of [4.3.3]Propellane-8,11-dione
✍ Pnina Ashkenazi; Moshe Kapon; Umberto Piantini; Wolfgang Von Philipsborn; David 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 247 KB 👁 1 views

## Abstract Oxidation of the title compound with __m__‐chloroperbenzoic acid affords a keto‐lactone, two bis‐lactones and a bis‐spirolactone, in varying amounts depending upon the reaction conditions. The structures were established by means of X‐ray diffraction, ^1^H‐ and ^13^C‐NMR spectroscopy.

Propellanes V. [3.3.1] Propellane
Propellanes V. [3.3.1] Propellane
✍ Philip Warner; Richard LaRose; Thomas Schleis 📂 Article 📅 1974 🏛 Elsevier Science 🌐 French ⚖ 181 KB
Preparation of Bicyclo[3.3.0]octane-2,8-
Preparation of Bicyclo[3.3.0]octane-2,8-dione- and Declain-1,8-dione-Derivatives
✍ Rudolf O. Duthaler; Peter Maienfisch 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 596 KB

## Abstract Alkylation of bicyclo[3.3.0]octane‐2,8‐dione (**1**), which is prepared by a modification of the procedure described in the literature, gives the methyl‐ and propynyl‐derivatives **6** and **7** (__Scheme 1__). In addition to the method described previously (__Scheme 2__), 9‐methyl‐__ci