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Open Access Oxidative Coupling of 6,6-Dimethylfulvenyl Anion

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Oxidative treatment of anion 1 (obtained by deprotonation of 6,6-dimethylpentafulvene) with CuCl2 gives a very complex mixture of coupling products 3 (18%), 4 (16%), 5 (36%), 6 (5%), and 7 (6%) (Scheme 2). This result shows that the reactive intermediate obtained by oxidation of 1 (which is believed to be fulvenyl radical 2) has several reactive sites. According to the experiments, reactivity is decreasing in the series C(7) > C(2)/C(3) > C(5) > C(1)/C(4) (Table 1), while simple frontier orbital considerations of radical 2 would suggest the sequence C(7) > C(5) > C(2)/C(3) > C(1)/C(4). The experimental result is in agreement with a considerable steric shielding of C(5) of 2.

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Document Type: Research Article

Publication date: September 1, 1992

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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