7, 7-Dimethyltricyclo[3.3.0.0.2, 8]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one

7, 7-Dimethyltricyclo[3.3.0.0.2, 8]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one

7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one (4) was prepared from 4, 4-di-methyl-2-cyclopentenone in several steps. The Birch reduction of 4 resulted in exclusive formation of a bicyclo[3.3.0]octanone (14)through C2-C8 bond clevage, while its substitutional reactions yielded bicyclo...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1988/04/25, Vol.36(4), pp.1351-1357
Hauptverfasser: IMANISHI, TAKESHI, YAMASHITA, MASAYUKI, MATSUI, MUNETAKA, NINBARI, FUSAKO, TANAKA, TETSUAKI, IWATA, CHUZO
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
SN2 reaction
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Zusammenfassung:7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one (4) was prepared from 4, 4-di-methyl-2-cyclopentenone in several steps. The Birch reduction of 4 resulted in exclusive formation of a bicyclo[3.3.0]octanone (14)through C2-C8 bond clevage, while its substitutional reactions yielded bicyclo[3.2.1]octanones (15) through C1-C2 bond cleavage as major products.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.36.1351