https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

Ionic liquids in catalysis

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

This Review describes the application of nitroxides to synthesis and polymer chemistry. The synthesis and physical properties of nitroxides are discussed first. The largest section focuses on their application as stoichiometric and catalytic oxidants in organic synthesis. The oxidation of alcohols and carbanions, as well as oxidative C-C bond-forming reactions are presented along with other typical oxidative transformations. A section is also dedicated to the extensive use of nitroxides as trapping reagents for C-centered radicals in radical chemistry. Alkoxyamines derived from nitroxides are shown to be highly useful precursors of C-centered radicals in synthesis and also in polymer chemistry. The last section discusses the basics of nitroxide-mediated radical polymerization (NMP) and also highlights new developments in the synthesis of complex polymer architectures.

Nitroxides: applications in synthesis and in polymer chemistry.

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

The silyl-Prins and aza-silyl-Prins reactions have been employed for the preparation of 6-CF3-substituted dihydropyrans and 6-CF3-substituted tetrahydropyridines. The product heterocycles have been further elaborated to a number of products, including CF3-substituted pipecolates and hydroxylated pyrans and piperidines.

Rapid Access to CF3‐Containing Heterocycles.

A versatile and high-yielding indium trichloride mediated cyclization reaction of silylated homoallylic alcohols, thiols, or amines with aldehydes or epoxides is described as a rapid route to a range of unsaturated heterocycles. The excellent diastereoselectivity observed offers a method of wide scope and generality.

/pdf/a-versatile-indium-trichloride-mediated-prins-type-reaction-47zs2y7hv1.pdf

A Versatile Indium Trichloride Mediated Prins-Type Reaction to Unsaturated Heterocycles.

Radical Reactions: Part 2

A simple methodology for the stereocontrolled synthesis of dihydropyrans has been established. The trans-dioxadecalin 22, featuring the middle portion of okadaic acid, has been efficiently assembled using this strategy. (C) 1997 Elsevier Science Ltd.

Concise and Stereocontrolled Assembly of Substituted Dihydropyrans. Synthetic Studies Towards the trans‐Dioxadecalin Subunit of Okadaic Acid.

[51766-21-3] C12H11ClNO2P (MW 267.66)





InChI = 1S/C12H11ClNO2P/c13-17(15,14-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H,(H,14,15)



InChIKey = ZUQYQPGYEFBITH-UHFFFAOYSA-N



(phosphorylating agent in oligonucleotide synthesis via the phosphotriester approach; for the conversion of acids to their symmetrical anhydrides and for the coupling of acids and amines to give amides; two important derivatives are also considered)



Physical Data: mp 132–134 °C.



Solubility: sol org solvents, e.g. acetone, dichloromethane.



Form Supplied in: white solid; widely available commercially.



Analysis of Reagent Purity: FT-IR;22 Rf (pure) = 0.63 (chloroform–acetone (5∶1) on silica).



Drying: is moisture sensitive; dry in vacuo (10−2 mmHg) over P2O5 at rt.



Preparative Methods: obtainable from phenyl phosphorodichloridate 2 and aniline (eq 1).1

(1)



Handling, Storage, and Precautions: irritant and moisture sensitive. May be harmful by inhalation (irritating to mucous membranes and upper respiratory tract), ingestion, or skin absorption. Incompatible with strong oxidizing agents and strong bases.

Adrian P. Dobbs

Papers

Rapid Access to CF3‐Containing Heterocycles.

A Versatile Indium Trichloride Mediated Prins-Type Reaction to Unsaturated Heterocycles.

Radical Reactions: Part 2

Concise and Stereocontrolled Assembly of Substituted Dihydropyrans. Synthetic Studies Towards the trans‐Dioxadecalin Subunit of Okadaic Acid.

Phenyl N‐Phenylphosphoramidochloridate