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

✍ Scribed by Ivanka Szele; Michal Tencer; Heinrich Zollinger

Publisher: John Wiley and Sons
Year: 1983
Tongue: German
Weight: 343 KB
Volume: 66
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19830660609

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✦ Synopsis

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).

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