Cyclopropanol, 1-methoxy

Dibromopropanones may also be reduced electrolytically to form cyclopropanone derivatives as illustrated by the formation 12> of 1-methoxytetramethylcyclopropanol, 38, and l-methoxy-2,2-dimethyl-cyclopropanol, 39, in excellent yields. 

Alkyl substituted cyclopropanols and cyclopropanone hemiacetals 115,116a) aiso undergo oxidative cleavage when exposed to air or peroxides the initial products are hydroperoxides such as 148. In the case of l-methoxy-2,2-dimethylcyclopropanol, the reaction can be followed by observing the emission peaks in the NMR spectrum, and these CIDNP effects have enabled identification of radical intermediates.1154) With di-f-butylperoxylate (TBPO), the isomeric radicals 143 and 144 are formed and these may undergo a diverse number of further reactions as indicated by the complex product mixture given in Table 20. 

With the exception of a few cyclopropanone hemiacetals, which are readily reduced with lithium aluminum hydride in diethyl ether to give the corresponding cyclopropanols, conversion of a cyclopropyl-oxygen bond to a cyclopropyl-hydrogen bond has only been achieved by reductive dealkoxylation of 1-alkoxycyclopropylamines where the alkoxy group is either methoxy or ethoxy 3. The reductions can be carried out with various hydrides, but the optimum reaction conditions in a specific case depend on the structure of the substrate. 

Cyclopropane derivatives have been prepared using alkenes, cm-dihalides, and copper. This is a convenient and useful procedure, e.g. cis-cyclo-octene was converted into bicyclo[6,l,0]nonane (77%) and into a mixture of endo- and cxo-9-methoxy-carbonylbicyclo[6,l,0]nonanes (71 % exo. endo = 1.3 1) using di-iodomethane and methyl dibromoacetate, respectively. An improved procedure for the conversion of alkenes into cyclopropanols uses lithium 2,2,6,6-tetramethylpiperidide and 2-chloroethyl chloromethyl ether, e.g. cycloheptene was converted into the 2-chloro-ethyl ether of bicyclo[5,l,0]octan-8-ol (62% exo.endo = 1.8 1). ... 

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