The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol—a new conformation of 1,3,2-dioxaphosphorinane ring

Kumar, K. Vasanth; Swamy, K. C. Kumara

doi:10.1016/j.carres.2007.02.031

Cited by 11 publications

References 27 publications

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Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo‐Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

Tamboli

Shashidhar

Gonnade

2015

Chemistry A European J

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Racemic 4-O-phenoxycarbonyl and 4-O-phenoxythiocarbonyl derivatives of myo-inositol orthoformate undergo thermal intramolecular cyclization in the solid state to yield the corresponding 4,6-bridged carbonates and thiocarbonates, respectively. The thermal cyclization also occurs in the solution and molten states, but less efficiently, suggesting that these cyclization reactions are aided by molecular pre-organization, although not strictly topochemically controlled. Crystal structures of two carbonates and a thiocarbonate clearly revealed that the relative orientation of the electrophile and the nucleophile in the crystal lattice facilitates the intramolecular cyclization reaction and forbids the intermolecular reaction. The correlation observed between the chemical reactivity and the non-covalent interactions in the crystal of the reactants provides a way to estimate the chemical stability of analogous molecules in the solid state.

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Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo‐Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

Tamboli

Shashidhar

Gonnade

2015

Chemistry A European J

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Rigid triol and diol with adamantane-like core derived from naturally occurringmyo-inositol and their polyaddition with diisocyanates

Okamoto

Onoue

Kobayashi

et al. 2014

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

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Two orthoester derivatives 1 and 2 that are easily accessible from naturally occurring myo-inositol were exploited as new triol-and diol-type monomers bearing a rigid adamantane-like structure to polyaddition with diisocyanates that gave the corresponding networked and linear polyurethanes. DSC analysis of the networked polyurethanes revealed their high glass transition temperatures ranging from 155 to 248 C, suggesting the contribution of the rigidity of the adamantane-like structure introduced at the nodes of the networked polyurethanes 6. Besides, the polyaddition of 2 with diisocyanates gave the corresponding linear polyurethanes 4, of which glass transition temperatures were high, ranging from 105 to 177 C, presumably by virtue of the rigidity of the adamantane-like structure introduced into the main chains. T g s of the networked polyurethanes 6 were higher than those of the linear polyurethanes 4.

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Spiro- and Tricyclic Phosphoranes with Six- and Higher-Membered Rings

Swamy

Pavan

Srinivas

2009

Topics in Heterocyclic Chemistry

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The first structural study on a cyclic tricoordinate phosphorochloridite and a pentacoordinate phosphorane based on 1,2,3,5-protected myo-inositol—a new conformation of 1,3,2-dioxaphosphorinane ring

Cited by 11 publications

References 27 publications

Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo‐Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo‐Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

Rigid triol and diol with adamantane-like core derived from naturally occurringmyo-inositol and their polyaddition with diisocyanates

Spiro- and Tricyclic Phosphoranes with Six- and Higher-Membered Rings

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