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Fulven-Dimere: Synthese, Strukturbeweis and thermisches Verhalten

✍ Scribed by Beat Uebersax; Markus Neuenschwander; Hans-Peter Kellerhals

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
845 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Fulvene‐Dieters: Synthesis, Structure Elucidation and Thermal Behaviour

In contrast to earlier assumptions, thermal reaction of pure fulvene (1a), 6‐methylfulvene (lb) and 6, 6‐dimethylfuivene (1c) at 227deg; gives oligomeric mixtures consisting mainly of the endo‐[4 + 2]‐eycloaddition products 2a, 2b and 2c. Thermal reactivity of the fulvenes decreases strongly in the series 1a > 1b > 1c. While the dimers 2b and 2c equilibrate very easily in solution above room temperature with 1b and 1c, respectively, 2a equilibrates with the isomer 5a (1, 6‐Dimethyliden3a α, 3bβ, 6a α, 6bβ‐tetrahydro‐1‐H), 6 H‐bi (cyclopentadienylen). This surprising rearrangement envolves a formal 1,3‐shift of the 1, 2‐dihydrofulvene‐unit of 2a (s. Scheme 4).

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