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Azulene–Naphthalene‐Type Rearrangements in Benz[ a ]azulene and Cyclohepta[ b ]indole
Author(s) -
Wentrup Curt,
Becker Jürgen
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603389
Subject(s) - azulene , chemistry , phenanthrene , naphthalene , indole test , flash vacuum pyrolysis , phenanthridine , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , pyrolysis
Flash vacuum pyrolysis (FVP) of benz[ a ]azulene yields phenanthrene and 2‐ethynylbiphenyl. FVP of cyclohepta[ b ]indole similarly yields phenanthridine and 2‐cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2‐ethynylbiphenyl and 2‐isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene–vinylidene mechanism of the azulene–naphthalene rearrangement, whereas other proposed mechanisms are ruled out.