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

Szele Ivanka | Zendy; Tencer Michal | Zendy; Zollinger Heinrich | Zendy

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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 ).

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