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Digitale Medien

Structure of a ring enlarged product from the base induced rearrangement of dibromomethylenebenzonorbornene (1996)

Balci, Metin ; Krawiec, Mariusz ; Ta§kesenligil, Yavuz ; [weitere]

Springer

Journal of chemical crystallography 26 (1996), S. 413-418

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ISSN: 1572-8854

Schlagwort(e): Cycloalkyne intermediates ; base-induced rearrangements ; ring expansion ; molecular mechanics ; Gaussian RHF/6-31G

Quelle: Springer Online Journal Archives 1860-2000

Thema: Geologie und Paläontologie , Physik

Notizen: Abstract The base-catalyzed rearrangement reactions of 2-bromomethylenebenzonorbornene8 and 2,2-dibromomethylenebenzonorbornene9 were studied. Reaction of8 with potassiumtert-butoxide in THF gave only the enol ether11 whose formation is rationalized via a carbene-cycloalkyne mechanism. However, treatment of9 with phenyllithium in THF at −40°C gave the ringenlarged dibromide13 whose structure is reported herein. The ring-enlarged product13 is rationalized in terms of carbanionic rearrangement. Quantum mechanical calculations are consistent with these observations.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1007/BF01665821

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Digitale Medien

Reactions of Benzocycloheptenes with Dienophiles (1991)

Adam, Waldemar ; Balci, Metin ; Ceylan, Zeynep ; [weitere]

Weinheim : Wiley-Blackwell

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

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ISSN: 0009-2940

Schlagwort(e): Diels-Alder reaction ; Cycloaddition ; Benzocycloheptenes ; Tetracyanoethylenes ; Triazolinediones ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 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.