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The Carbon Zip Reaction: A Method for Expanding Carbocycles (1983)

Nakashita, Yoshihiko ; Hesse, Manfred

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 66 (1983), S. 845-860

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A general method for enlargement of carbocyclic rings by the so called zip reaction is given. The Michael adducts of 2-nitrocycloalkanones with 3-oxo-4-pentenoates in the presence of tetrabutylammonium fluoride give in high yield compounds with the ring enlarged by four C-atoms. By this method 7-, 8-, and 12-membered cycloalkanones were converted respectively to 11-, 12-, and 16-membered functionalized carbocycles (see Scheme 2 and 3).

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19830660318

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