The photomediated reaction of alkynes with cycloalkanes

Doohan, Roisin; Hannan, John J.; Geraghty, Niall W. A.

doi:10.1039/b517631j

Cited by 27 publications

(18 citation statements)

References 54 publications

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“…Methyl cyclobutenecarboxylates 4–6 a and related norbornene‐derived compounds 7–9 a were prepared following the reported procedure . 2‐Methoxyethyl propiolate 2 was prepared via Mitsunobu esterification of propiolic acid with 2‐methoxyethanol. Preparation of 3‐γ‐butyrolactonyl propiolate 3 was reported in our previous publication …”

Section: Methodsmentioning

confidence: 99%

Radical copolymerization of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework with alkyl (meth)acrylates

Ihara

Ueda

Yokoyama

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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Radical copolymerization behavior of alkyl cyclobutenecarboxylate‐derivatives 4‐6 and related norbornene‐derived compounds 7–9 is described. A variety of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework (4–6) were prepared by [2 + 2] cycloaddition of five, six, and eight‐membered cycloolefins with alkyl propiolates [alkyl = Me, 2‐hydroxyethyl, and 3‐γ‐butyrolactonyl (γ‐BL)]. The fused cyclobutenecarboxylates 4–6 were radically copolymerized with n‐butyl acrylate (nBA) to afford random copolymers, and terpolymerized with alkyl methacrylates with bulky ester groups [alkyl = γ‐BL and 3‐(3‐methyladamantyl)]. The cyclobutane‐containing bicyclic framework incorporated in the resulting polymer backbone contributes to raising Tg of resulting copolymers. Similar results were obtained when a mixture of related norbornene‐derived compounds were used as monomers with an apparently enhanced Tg‐raising effect in the copolymerization with nBA. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2716–2724

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Section: Methodsmentioning

confidence: 99%

Radical copolymerization of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework with alkyl (meth)acrylates

Ihara

Ueda

Yokoyama

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…70:30 from the corresponding aldehydes 12a-e by Horner-Wadsworth-Emmons olefination employing ethyl (di-o-tolylphosphono)acetate (Scheme 3). Subsequent reduction to the respective allyl alcohol with DIBAL in THF at -78°C, followed by oxidation with MnO 2 in hexane at room temperature gave the target (2Z)-alkenals (Z)-10a, [28] (Z)-10b, [29] and (Z)-10c-e.…”

Section: Synthesis Of (Z)-αβ-unsaturated Aldehydes (Z)-10a-ementioning

confidence: 99%

Stereoselective Synthesis of (2E,4Z)‐Dienamides Employing (Triphenylphosphoranylidene)ketene

et al. 2009

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The three-component reaction between ylide Ph 3 PCCO, amines and aldehydes is known to afford selectively (E)-α,β-unsaturated amides. We applied a variant of this methodology to the preparation of (2E,4Z)-dienamides 11 utilizing the phosphonium salt formation from ethyl 5-aminopentanoate hydrochloride and Ph 3 PCCO followed by deprotonation with DBU and a Wittig olefination of the corresponding ylide with

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“…The reaction involves the regiospecific addition of a photochemically generated cycloalkyl radical to the β ‐carbon of the alkyne. [ 80 ]…”

Section: Synthetic Strategies Of Acrylonitrilesmentioning

confidence: 99%

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

Tan

Zengin

2021

Archiv der Pharmazie

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Acrylonitrile is a fascinating scaffold widely found in many natural products, drugs, and drug candidates with various biological activities. Several drug molecules such as entacapone, rilpivirine, teriflunomide, and so forth, bearing an acrylonitrile moiety have been marketed. In this review, diverse synthetic strategies for constructing desired acrylonitriles are discussed, and the different biological activities and medicinal significance of various acrylonitrile derivatives are critically evaluated. The information gathered is expected to provide rational guidance for the development of clinically useful agents from acrylonitriles.

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The photomediated reaction of alkynes with cycloalkanes

Cited by 27 publications

References 54 publications

Radical copolymerization of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework with alkyl (meth)acrylates

Radical copolymerization of alkyl cyclobutenecarboxylates fused with cycloaliphatic framework with alkyl (meth)acrylates

Stereoselective Synthesis of (2E,4Z)‐Dienamides Employing (Triphenylphosphoranylidene)ketene

Insights into the chemistry and therapeutic potential of acrylonitrile derivatives

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