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Tandem Ring Enlargement by Two Carbon Units from the Bicyclo[3.3.0]octane to the Bicyclo[5.5.0]dodecane System (1999)

Dehmlow, Eckehard Volker ; Heitkamp, Thomas ; Sielemann, Dirk

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 3135-3138

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ISSN: 1434-193X

Schlagwort(e): Bicyclo[5.5.0]dodecatetraene derivatives ; Ring enlargement, 5-membered → 7-membered ; [1,5]-H shift ; Polycycle by twofold Michael addition ; Adducts of enamines and alkynoic esters ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Reaction of the bis(enamines) 2b and 3bwith acetylenedicarboxylic ester gave stable tetracyclic compounds 4b and 5b. The related compound 3a, however, led to bicyclo[5.5.0]dodecatetraenes 6a, 6b, and 7a/7b directly. 7a/7b are interrelated by a rapid [1,5]-H shift, whereas 6a and 6b do not rearrange. Hydrolysis of 6b yielded the novel cage compound 10 by dual intramolecular Michael addition.

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

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Digitale Medien

Unusual reactions between chloroketenes and 1,3,5-tri-tert-butylcyclopentadiene (1995)

Dehmlow, Eckehard Volker ; Bollmann, Christof ; Neumann, Beate ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1995 (1995), S. 1915-1919

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ISSN: 0947-3440

Schlagwort(e): Bicyclo[3.2.0]heptenones ; Complex rearrangements ; Cyclopentadiene, acylation ; Formal Diels-Alder reaction, ketene-cyclopentadiene ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Reaction of title compound 1 with dichloroketene resulted in a complex rearrangement to 2 when the ketene was generated from Cl3CCOCl/Zn. In contrast, treatment of 1 with the ketene produced from dichloroacetyl chloride/triethylamine gave a bicyclo[3.2.0]heptenone (3) along with acylation product 4. Reaction of monochloroketene with 1 afforded the „normal“ endo-chloro compound 6 which thermally rearranged to the formal Diels-Alder product 7.

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.1995199511270

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