Reactions of Benzocycloheptenes with Dienophiles | Zendy

Adam Waldemar | Zendy; Balci Metin | Zendy; Ceylan Zeynep | Zendy; Hinz Ricardo Francisco | Zendy

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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 .

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