Methods for Vinyl Ether Synthesis

Abstract

Deceptively simple as the structure may appear, there is no single general method by which to synthesize the vinyl (enol) ether functionality. However, there exists a diverse array of complementary methods by which this functionality has been achieved. This review presents the scope and limitations of these methods according to reaction type, specifically via ether modifications, elimination reactions, carbonyl olefinations, alcohol additions and carbon-oxygen coupling reactions.

TEMPO-Catalyzed Direct Conversion of Primary Alcohols to α-Chloroacetals with TCCA Both as an Oxidant and a Chlorination Reagent

“…In the second stage of the research, the α-chloroacetals were successfully transformed into enol ethers in the presence of sodium (Scheme 2). In the literature, there have been various methods 22 for preparing enol ethers such as vinyl transfer to alcohols, 23 reduction of vinyl phosphate ethers, 24 functionalization of vinyl ethers, 25 and so on. A method closely related to this work is the reaction between 3-chloro-2-methoxytetrahydropyran with sodium to yield chain enol ether with hydroxyl group.…”

Recent advances in applications of vinyl ether monomers for precise synthesis of custom-tailored polymers

“…Due to their low toxicity [58] and efficient manufacturing, vinyl ethers have been extensively used in research and industry without any significant amendments to the concept of their synthesis [59,60]. A number of modifications have been introduced, including variation of eliminating agents [61], upgrade of the catalysts and conditions for trans-vinylation processes [62][63][64][65], adjustment of the solvents and expansion of the substrate scope for the addition technique [66,67].…”

An efficient access to functionally substituted 1,3-oxazolidin-2-ones via cyclization of 1-alkylamino- and 1-arylamino-3-[2-(vinyloxy)ethoxy)]propan-2-ols with dimethyl carbonate

“…cycloadition, 19 hydroformylation, 20 metathesis, 21 Heck reaction 22 ) for synthesis of complex organic molecules. 23,24 Therefore, the introduction of the highly reactive vinyloxy fragment into the structure of oxazolidin-2-one allows to expand the scope of their applications as building blocks and monomers for organic chemistry.…”