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Article << Previous     |     Next >>   Contents Vol 58(5)

Some Stability and Stereochemical Considerations of Simple Bicyclo[4.2.0]octanols

Wendy A. Loughlin A B, Catherine C. Rowen A, Michelle A. McCleary A

A School of Science, Eskitis Research Institute, Griffith University, Brisbane QLD 4111, Australia.
B Corresponding author. Email: w.loughlin@griffith.edu.au
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Bicyclooctanols 3 and 4 were formed with control of the stereochemistry at C8 by using an aluminium enolate of cyclohexanone in 1,2-dimethoxyethane. Bicyclooctanols 1 and 3 were stable towards aqueous hydrochloric acid for short times (< 3.5 h), and ring open to a diastereomeric mix of monoalkylated 5 under protic or aprotic conditions in the presence of base (NaOH or lithium diisopropylamide). The rate of ring opening appears to be dependent on reaction temperature. Bicyclooctanols 1, 3, and 4 displayed remarkable stability when heated at reflux in benzene, whereas use of ethanol prompted stereoselective ring opening of 1 and 3 to give individual diastereomers of monoalkylated 5 and ring opening of 4 to give a 50 : 50 mix of diastereomers of 5. This unexpected result was attributed to the stereochemistry of the bicyclooctanol and placement of hydrogen-bonding sites.

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