R -8-Hydroxynonyl-l, 3-dioxolane

Reactions of organomagnesium compounds with substituted oxiranes 

An analogous reaction of 2-(5-bromopentyl)-l,3-dithiane is described, giving 2-[(R)-7-hydroxyoctyl]-l,3-dithiane (70%). 

Reactions of Grignard reagents with oxetane lead to three-carbon homologation yields are often good, but 3-halogenopropanol may be a significant by-product [37]  

Copper(i) catalysis is also reported to be beneficial for this reaction [9,36], Organomagnesium compounds are much less reactive than organolithium compounds [G] towards THF, but the reaction of triphenylmethylmagnesium bromide with THF can give high yields of 5,5,5-triphenylpentan-l-ol [38]. 

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