ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Fulvene-Dieters: Synthesis, Structure Elucidation and Thermal BehaviourIn 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).
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650109
Permalink