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Functionalized Cycloheptanes from Bicyclo[4.2.1]nonanes (1984)

Huston, Rima ; Rey, Max ; Dreiding, André S.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 67 (1984), S. 1506-1514

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Several oxidative, reductive and C,C-cleavage reactions were performed starting from the three bicyclo[4.2.1]nona-3,7-diene-2-one derivatives 1, 5 and 18. The oxidations were selective and led to the diols 2,8 and 9, and the epoxides 6,9, and 20. The reductions were selective only in the case of 20 21; otherwise they led to mixtures of the alcohols 10 and 11, and of the dienes 14 and 15. The periodate ring cleavages afforded the functionalized cycloheptane derivatives 3, 12, 13 and 16. Configurational assignments were made on the basis of detailed 1H-NMR and X-ray analysis of 20.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19840670614

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