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Reactions of bicyclobutylidene and 1,3-bis(trimethylene)propadiene : Synthesis of trispiro[3.0.3.0.2.0]undecane, 9-methylenedispiro[3.0.3.1]nonane, and bicyclobutylidene-2,2'- and 2,4'-dione

✍ Scribed by Lim Keow Bee; John W. Everett; Peter J. Garratt

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
824 KB
Volume
33
Category
Article
ISSN
0040-4020

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The dispiroketones 46 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the [3.3.3]propellane 37 under thermodynamic control. The corresponding alcohols 10-12 all yield the [3.3.3]propeUane 41. The rearrangement of [7,7-D2)-12 to [8

2,7,9-trimethylenetricyclo[4.3.0.03,8]no
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✍ Gleiter, Rolf ;Herb, Thilo ;Borzyk, Oliver ;Hyla-Kryspin, Isabella 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 776 KB

## Abstract The synthesis of 2,7,9‐trimethylenetricyclo[4.3.0.0^3,8^]nonane (8), 7,9‐dimethylenetricyclo[4.3.0.0^3,8^]nonan‐2‐one (15), and 2,9‐dimethylenetricyclo[4.3.0.0^3,8^]non‐4‐ene (9) has been achieved. The first key step of the synthesis is a Diels‐Alder reaction. In the reaction sequence a