Use of iodobenzene diacetate for the synthesis of α-iodoepoxides

Galatsis, Paul; Millan, Scott D.

doi:10.1016/0040-4039(91)80515-8

Cited by 40 publications

(16 citation statements)

References 16 publications

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“…A useful synthetic methodology is based on transformations of the alkoxy radicals generated by the reaction of alcohols with DIB and iodine under photochemical or thermal conditions. This methodology has been utilized in a number of syntheses. ,− In particular, the preparation of modified cyclodextrin 286 by an intramolecular radical approach from alcohol 285 using the DIB–iodine system was reported by Martin and Suarez (Scheme ). …”

Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C−C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.

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Section: Synthetic Applications Of Trivalent Iodine Compoundsmentioning

confidence: 99%

Advances in Synthetic Applications of Hypervalent Iodine Compounds

2016

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“…Because HVICs can alkylate or ligand exchange with many H-labile species, molecular iodine also promotes the hypoiodite reaction ,, of alcohols, ,− , carboxylic acids, ,− and amines. − This constitutes another unusual source of radicals, as the resulting transient R–Y–I − iodinated species photolyzes under UV–vis irradiation to generate the corresponding R–Y • (Y = O, COO, and NH) radicals.…”

Section: Controlled Radical Polymerization Of Vdfmentioning

confidence: 99%

“…Consequently, RCOOI intermediates have found use in Hunsdieker-like photohalodecarboxylative reactions, or in halogenations with IDAB, IFAB, or their ligand-exchanged HVIC congeners in the presence of R–I ,, or I 2 . ,− ,− ,, However, they have never been employed in trifluoromethylations or polymerization reactions.…”

Section: Controlled Radical Polymerization Of Vdfmentioning

confidence: 99%

Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride

2016

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This review summarizes recent research on novel photochemical methods for the initiation and control of the polymerization of main chain fluorinated monomers as exemplified by vinylidene fluoride (VDF) and for the synthesis of their block copolymers. Such reactions can be carried out at ambient temperature in glass tubes using visible light. Novel, original protocols include the use of hypervalent iodide carboxylates alone or in conjunction with molecular iodine, as well as the use of photoactive transition metal carbonyls in the presence of alkyl, fluoroalkyl, and perfluoroalkyl halides. An in-depth study of the reaction parameters highlights the use of dimethyl carbonate as a preferred polymerization solvent and outlines the structure-property relationship for hypervalent iodide carboxylates and halide initiators in both the free radical and iodine degenerative transfer controlled radical polymerization (IDT-CRP) of VDF. Finally, the rational selection of metal carbonyls that are successful not only as IDT mediators but, more importantly, in the quantitative activation of both PVDF-CH2-CF2-I and PVDF-CF2-CH2-I chain ends toward the synthesis of well-defined PVDF block copolymers is presented.

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“…The electrophilic allyloxy radicals could be efficiently reduced by Bu 3 SnH 4. 5 Iodo epoxides could be obtained from the exposure of allyl alcohols to electrophilic radical traps such as mercury oxide and iodine (Scheme )6 or to diacetoxyiodobenzene and iodine 7…”

Section: Epoxide Oxetane and Aziridine Opening Through Generatiomentioning

confidence: 99%

Strained Heterocycles in Radical Chemistry

2003

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Over the last few decades the use of radicals in synthesis has witnessed an explosive growth through introduction of efficient chain and electron-transfer reactions. Strained heterocycles, in particular, have emerged as a highly versatile and readily available class of radical precursors. The generation of carbinyl radicals of heterocycles has resulted in many elegant applications of heteroatom-centered radicals, such as beta fragmentations, cyclizations, and intramolecular hydrogen atom abstractions. Direct electron transfer to strained heterocycles has been realized through the use of arene radical anions. The method combines the virtues of radical and organometallic chemistry to yield useful functionalized organolithium compounds. Epoxides have been opened with high regioselectivity by titanocene(III) reagents in either stoichiometric or catalytic quantities to yield beta-titanoxy radicals. This development has resulted in many new applications in natural product synthesis.

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Use of iodobenzene diacetate for the synthesis of α-iodoepoxides

Cited by 40 publications

References 16 publications

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Advances in Synthetic Applications of Hypervalent Iodine Compounds

Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride

Strained Heterocycles in Radical Chemistry

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