1,2-Cyclooctane diol

This epoxide has been found to be particularly useful in the laboratory in the large-scale preparation of frarty-cyclooctene using the procedure of Whitham.14 trans-Cyclooctane- 1,2-diol is obtained from cis-cyclooctene oxide on treatment with sodium acetate in acetic acid and alkaline hydrolysis of the intermediate trans-2-acetoxycyclooctanol. The trans diol is converted to its benzal-dehyde acetal, which on treatment with butyllithium affords trans-cyclooctene in a stereospecific manner. 

An nnnsnal ring-contraction reaction occnrs on the acid-catalyzed interaction of trimeth-ylhydroqninone 144 with cycloalkane-1,2-diols (e.g. 145) to form the spiro componnds 146 (eqnation 67) . Besides two isomers of cyclohexane-1,2-diols 145, this rearrangement was also described for cyclopentane-, cycloheptane- and cyclooctane-1,2-diols . 

This variation of the Corey-Winter reaction is not stereoselective thus the thionocarbonates of either cis- or fra/ji-cyclooctane-1,2-diol give only cis-cyclooctene. 

Cyclooctadiene-1,5, 23, 62, 445 Cyclooctane-1,2-diol, 384 Cyclooctane-1,5-diol, 64 Cyclooctanol, 183 Cyclooctatetraene, 23 Cyclooctatetraene epoxide, 306, 519 Cyclooctatetraeneiron tricarbonyl, 567 Cyclooctene, 23, 183, 445 Cyclooctene oxide, 334 Cyclooctyl fluoride, 183 Cyclopentadiene, 123, 291 Cyclopentadienone, 454 iT-CycIopentadienylcobalt dicarbonyl, 153-154... 

Syn-hydroxylation of olefins has also been carried out with KMnO solution using a PTC catalyst under alkaline conditions. Thus, under alkaline conditions, cyclooctene gives 50% yield of cis 1,2-cyclooctane diol compared to an yield of about 7% by the classical technique (Scheme 72). 

The central bond of bicyclo[4.2.0]octane-l,6-diol was cleaved by potassium periodate in water at room temperature to yield cyclooctane-1,4-dione.156... 

A convenient synthesis of cyclopropanol involves the reaction of propargyl bromide with 2 moles of 9-BBN in THF sodium hydroxide or methyllithium is then added. B-Cyclopropyl-9-borabicyclo[3.3.1]nonane is obtained in 70% yield. Oxidation with hydrogen peroxide (sodium acetate) in the usual way affords cyclopropanol (65% yield) and cis-cyclooctane-1,5-diol.9... 

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