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Synthesis 1999; 1999(5): 854-858
DOI: 10.1055/s-1999-3483
DOI: 10.1055/s-1999-3483
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© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Synthesis of Several 8-Halopentacyclo[6.4.0.02,10.03,7.04,9]dodecane Derivatives
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Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synthesis/199905/lookinside/thumbnails/10.1055-s-1999-3483-1.jpg)
The synthesis of pentacyclo[6.4.0.02,10.03,7.04,9]dodecane-8-carboxylic acid (7) from the known pentacyclo[6.4.0.02,10.03,7.04,9]dodecane-8,9-dicarboxylic acid (2) and its halodecarboxylation to the 8-bromo- (6), 8-chloro- (11) and 8-iodo- (10) derivatives is described. Hydrolysis of the methyl ester of 7 (5) with conc. sulfuric acid at around 90 °C gives the rearrangement product, 8-hydroxypentacyclo[6.5.0.02,11.03,7.04,10]tridecan-9-one (8).
8-chloro-(or 8-bromo or 8-iodo)pentacyclo [6.4.0.02,10.03,7.04,9]dodecane - 8-hydroxypentacyclo[6.5.0.02,11.03,7.04,10]tridecan-9-one - iodosobenzene diacetate - halodecarboxylation - rearrangement