Epoxides and Oxiranes

The principal side reaction to epoxide coupling is hydrolysis. Particularly at acid pH values, the epoxide ring can hydrolyze to form adjacent hydroxyls. This diol can be oxidized with periodate to create a terminal aldehyde residue with loss of one molecule of formaldehyde (Chapter 1, Section 4.4). The aldehyde then can be used in reductive amination reactions. The reaction of an epoxide group with an ammonium ion generates a terminal primary amine group that also can be used for further derivatization. 

The coupling reaction of a carbonate functional group with an amine is best done in slightly alkaline pH (7-9) and in the absence of any competing amine or sulfhydryl components. 

Nucleophiles, such as the primary amino groups of proteins, can react with the 

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Pages, X., C. Bonnet, and J. Laur, Synthesis of New Derivatives from High-Oleic Sim-flower Methyl Esters via Epoxidation and Oxirane Opening, Presented during the 1998 AOCS Annual Meeting, Chicago, IL. 

Synthesis of New Derivatives from Vegetable Oil Methyl Esters via Epoxidation and Oxirane Opening... 

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