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Reactions of Benzocycloheptenes with Dienophiles
Author(s) -
Adam Waldemar,
Balci Metin,
Ceylan Zeynep,
Hinz Ricardo Francisco
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240222
Subject(s) - tetracyanoethylene , cycloaddition , chemistry , medicinal chemistry , bicyclic molecule , stereochemistry , organic chemistry , catalysis
The Diels‐Alder reactions of 5H ‐benzocycloheptene ( 1 ) with tetracyanoethylene (TCNE) afforded the [2+2] and [4+2] cycloadducts 7, 8 , and 10 and the benzodicyanoheptafulvalene 9 . The norcaradiene product 10 was synthesized independently by cycloaddition of TCNE to 7H ‐benzocycloheptene ( 3 ). The addition of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (MTAD) to 3 gave bis‐urazole 13 , which was formed by ene reaction followed by [4+2] cycloaddition. The spirocycloheptatriene 15 gave with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD) the bisurazole 16 .