Reaction between 2-phenyl-1,3-benzodioxole and n-butyl-lithium; an unsuccessful attempt to synthesize benzyne

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Abstract
2-Phenyl-1,3-benzodioxole (1) on treatment with n-butyl-lithium in hexane did not fragment to give benzyne. Instead o-(1 -phenylpentyloxy) phenol (3), catechol, and cis- and trans-1 -phenylpent-1 -ene (2) were obtained. A mechanism for the formation of these products is suggested.

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