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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
Author(s) -
Szele Ivanka,
Tencer Michal,
Zollinger Heinrich
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660609
Subject(s) - chemistry , methanol , deuterium , medicinal chemistry , fluorene , aryl , ion , photochemistry , organic chemistry , polymer chemistry , polymer , alkyl , physics , quantum mechanics
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 ).