Metallic nickel-assisted room-temperature generation and Diels-Alder chemistry of o-xylylene intermediates

S Inaba, RM Wehmeyer, MW Forkner…

Index: Inaba, Shin-ichi; Wehmeyer, Richard M.; Forkner, Matthew W.; Rieke, Reuben D. Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 339 - 344

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Citation Number: 49

Abstract

Highly reactive metallic nickel, prepared by the lithium metal reduction of nickel iodide using naphthalene as an electron carrier, was found to induce 1, 4-dehalogenation of a, a'-dihalo- o-xylene derivatives at room temperature. The reaction proceeds in the presence of a variety of electron-deficient olefins, giving Diels-Alder cycloadducts in moderate to good yields presumably via the highly reactive intermediate o-xylylene 2. 1, 3-Dibromoindan and 1, 4- ...

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