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Formation of 5-Hydroxy-indan-2-one from Attempts to Hydrolyse 9-Ethylenedioxy-bicyclo[3.3.1]nonane-3,7-dione

✍ Scribed by Christopher B. Chapleo; André S. Dreiding

Publisher: John Wiley and Sons
Year: 1977
Tongue: German
Weight: 238 KB
Volume: 60
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19770600437

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✦ Synopsis

Bildung von 5‐Hydroxy‐indan‐2‐on bei Hydrolyseversuchen mit 9‐Äthylendioxy‐bicyclo[3.3.1]nonan‐3,7‐dion

Verschiedene Versuche, 9‐Äthylendioxy‐bicyclo[3.3.1]nonan‐3,7‐dion (2) durch Hydrolyse in das entsprechende Triketon 3 umzuwandeln, führten nur zu 5‐Hydroxy‐indan‐2‐on (4) und in einem Fall auch noch zu etwas 7,9‐Bis(äthylendioxy)‐bicyclo‐[3.3.1]nonan‐3‐on (5). Unter milderen Hydrolysebedingungen reagierte 2 gar nicht.

Die Bildung von 4 aus 2 wird über eine Wagner‐Meerwein‐Umlagerung und nach‐folgende Eliminierung von Äthylenglycol formuliert. Das so entstandene Äthylenglycol reagiert mit noch vorhandenem Acetal 2 zum Bis‐acetal 5, was als weitere Bestätigung der Resistenz von 2 gegen Hydrolyse gelten darf.

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