Boric acid mediated preparation of mesocyclic thiocrown ethers containing xylylene units. Molecular structures of 3,8-dibenzo-1,6-di-thiacyclodecane and 2,5,8-trithia-(9)-p-benzenophane
| Autor: | J. J. H. Edema, H. Thijs Stock, Wilberth J. J. Smeets, Anthony L. Spek, J. Buter, Richard M. Kellogg |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 1993 |
| Předmět: |
BORIC ACID
Base (chemistry) Stereochemistry METAL COMPLEXES COPPER(I) METHYLMERCURY SILVER(I) COMPLEXES Biochemistry Medicinal chemistry HEXATHIA-18-CROWN-6 Boric acid chemistry.chemical_compound TEMPLATE Crystal data Drug Discovery CRYSTAL-STRUCTURES Xylylene THIOCROWN ETHERS CYCLIC SULFIDES chemistry.chemical_classification Organic Chemistry Dithiol CROWN THIOETHER CHEMISTRY 14-HEXATHIACYCLOHEXADECANE 16S6 chemistry Yield (chemistry) 1 4 7-TRITHIACYCLONONANE POLYTHIOETHERS 7-TRITHIACYCLONONANE 1 3 6 9 11 14-HEXATHIACYCLOHEXADECANE 16S6 |
| Zdroj: | Tetrahedron, 49(20), 4355-4364. PERGAMON-ELSEVIER SCIENCE LTD |
| ISSN: | 0040-4020 |
| Popis: | Reaction of a dithiol with B(OH)3 and base in MeOH followed by reaction with xylylene dibromides proceeds selectively to give the corresponding ortho, meta or para-cyclophanes in good yield (70-86 %). The syntheses of examples of all three types of benzenophanes are discussed. The molecular structures of 3,8-dibenzo-1,6-dithiacyclodecane (8) and 2,5,8-trithia-(9)-p-benzenophane (5) have been determined by X-ray crystallography. Crystal data for 8: space group P2(1)/c with a=8.2745(10), b=4.9330(10), c=16.5500(12) A, beta=100.37 (1)-degrees, Z=2; R=0.043 (R(w)=0.045) for 949 reflections (I>2.5 sigma (I)). Crystal data for 5 (150K): Space group P2(1)/c with a=10.310(1), b=7.430 (1), c=17.681(2) A, beta=113.27(1)-degrees, Z=4; R=0.065 (R(w)=0.065) for 1969 reflections (I>2.5 sigma(I)). |
| Databáze: | OpenAIRE |
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