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Reactions of Benzocycloheptenes with Dienophiles (1991)

Adam, Waldemar ; Balci, Metin ; Ceylan, Zeynep ; [et al.]

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 383-386

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ISSN: 0009-2940

Keywords: Diels-Alder reaction ; Cycloaddition ; Benzocycloheptenes ; Tetracyanoethylenes ; Triazolinediones ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19911240222

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