Chemistry of ((Perfluoroalkyl)methyl)oxiranes. Regioselectivity of Ring Opening with O-Nucleophiles

What is it about?

Lewis acid catalyzed reactions of fluoroalkyloxiranes such as (I) with alkanols and 2-hydroxyethyl acrylates take place at the terminal carbon atom to furnish the ring-opened products (III) with complete regioselectivity. Contrary to this selective reaction, oxirane ring opening with methacrylic acid in the presence of Et3N provides two regioisomeric products (V) and (VI). The epoxides (I) can be easily converted into the corresponding diols (cf. (IX)) via dioxolane intermediates (VIII). The reaction of the epoxides with thiourea gives the corresponding thiiranes (XIII). The obtained methacrylates (e.g. ( IIId), (IIIe), (V), and (XI)) represent new types of amphiphilic monomers.

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Why is it important?

Lewis acid catalyzed reactions of fluoroalkyloxiranes such as (I) with alkanols and 2-hydroxyethyl acrylates take place at the terminal carbon atom to furnish the ring-opened products (III) with complete regioselectivity. Contrary to this selective reaction, oxirane ring opening with methacrylic acid in the presence of Et3N provides two regioisomeric products (V) and (VI). The epoxides (I) can be easily converted into the corresponding diols (cf. (IX)) via dioxolane intermediates (VIII). The reaction of the epoxides with thiourea gives the corresponding thiiranes (XIII). The obtained methacrylates (e.g. ( IIId), (IIIe), (V), and (XI)) represent new types of amphiphilic monomers.

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