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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

Keywords: 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

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

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