Reactions of Alkenediazonium Salts. Part 2. Methanolysis of 2,2(2′,2″‐biphenylylene)ethene‐1‐diazonium hexachloroantimonate. A rearrangement to 9‐methoxyphenanthrene

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Abstract
The title compound (1) reacts with excess methanol forming a rearranged product, 9‐methoxyphenanthrene (2). 9‐(Methoxymethylidene)fluorene (4) does not rearrange to give 2 under the same conditions. In deuterated methanol no labelled product is obtained, showing that the possible mechanism involves either the formation of a primary vinyl cation 5 rearranging to an aryl cation 6 or the formation of a β‐alkoxycarbene (12), which rearranges to an arene. The results obtained are compared with previously reported reactions, which were postulated to proceed via a 2,2(2′,2″‐biphenylylene)ethene‐1‐diazonium ion (23).