Epoxide reaction with acids

Epoxides can also be opened by reaction with acids other than H30+. If anhydrous HX is used, for instance, an epoxide is converted into a trans halohydrin. 

High-level calculations of aUtene epoxidation reactions with peroxyformic acid, HO—O (C=0)H, which is isoelectronic with peroxynitrous acid [HO—0(N=0)], have indicated... 

The reactions of Grignard reagents with aldehydes and ketones give alcohols, reaction with acid chlorides and esters give tertiary alcohols, reaction with carbon dioxide to give carboxylic acids, reaction with nitriles give ketones, and reaction with epoxides give alcohols. 

The target compound contains a reactive epoxide ring. Epoxides react with acids and bases, and the epoxide might not survive the crucial ether-forming reaction just shown. Perhaps the epoxide is best added after formation of the ether. That gives us the following final two steps in the synthesis ... 

In addition to their reactions with acid chlorides, epoxides, and a,P-unsaturated carbonyl compounds (Sections 20.13-20.15), organocuprate reagents (R2CuLi) also react with organic halides R X to form coupling products R-R that contain a new C-C bond. Only one R group of the organocuprate is transferred to form the product, while the other becomes part of RCu, a reaction by-product. 

In summary, epoxides are produced not only as endproducts, but also as intermediates because they are valuable building blocks in synthetic organic chemistry [82-84] (Table 1.3). Until recently, epoxide intermediates were produced by direct oxygen transfer to olefins by a variety of stoichiometric methods. Recently, considerable efforts have been made to conduct the transformations selectively under catalytic conditions. Because epoxides are reactive substances, they can undergo diverse transformations by reactions with acids and bases, and their reactivity has been exploited to form a diverse range of products by so-called click chemistry [85,86], which combines the breadth of combinatorial methods with the precise synthesis of organic chemistry. 

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