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Some stability and stereochemical considerations of simple Bicyclo[4.2.0]octanols
Journal article   Peer reviewed

Some stability and stereochemical considerations of simple Bicyclo[4.2.0]octanols

W.A. Loughlin, C.C. Rowen and M.A. McCleary
Australian Journal of Chemistry, Vol.58(5), pp.354-361
2005
DOI: https://doi.org/10.1071/CH04288
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Abstract

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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Source: InCites

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Citation topics
2 Chemistry
2.1 Synthesis
2.1.40 Total Synthesis
Web Of Science research areas
Chemistry, Multidisciplinary
ESI research areas
Chemistry
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