Synthesis of Dihydrothiophene, Thiophene, and Their Selenium Analogues Carrying Four Phosphoryl Groups
- 1 April 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (9), 1729-1732
- https://doi.org/10.1021/ol070414y
Abstract
Sodium hydrosulfide undergoes addition to two molecules of bis(diethoxyphosphoryl)acetylene followed by cyclization to give a 2,3-dihydrothiophene carrying four phosphoryl groups. Oxidation of the 2,3-dihydrothiophene with mCPBA gives the corresponding sulfoxide or sulfone depending on the ratio of the reagents, and the sulfoxide is dehydrated to afford a tetraphosphorylthiophene. The corresponding dihydroselenophene and selenophene are also synthesized in a similar manner.Keywords
This publication has 28 references indexed in Scilit:
- (η5-Cyclopentadienyl)(η4-di- and tetra-phosphorylcyclobutadiene)cobalt(i): Synthesis, structure, and formation of 1-D coordination polymerChemical Communications, 2002
- Octaethyldiphosphaferrocene: An Efficient Ligand in the Palladium-Catalyzed Suzuki Cross-Coupling ReactionOrganometallics, 2000
- Dialkyl 1-Alkynylphosphonates: a Range of Promising ReagentsEuropean Journal of Organic Chemistry, 2000
- Synthesis and characterization of pentakis(dimethylphosphanyl)cymantrene [Mn{C5(PMe2)5}(CO)3], the first cyclopentadienyl complex with five phosphanyl substituents †J. Chem. Soc., Dalton Trans., 1999
- Preparation, Properties, and Reactions of Metal‐Containing Heterocycles, XCV. Transition‐Metal‐Mediated Cyclocotrimerization of Selenophosphinites with Activated AlkynesEuropean Journal of Inorganic Chemistry, 1996
- First Synthesis of Selenophene 1,1-DioxidesChemistry Letters, 1996
- Oxidation of Tetraarylselenophenes and Benzo[b]selenophene with m-Chloroperbenzoic AcidChemistry Letters, 1995
- 2,2′-Bitellurophene and 2,2′:5′,2″-Tertellurophene as Novel High Homologues of TelluropheneTetrahedron Letters, 1994
- Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of HeterocyclesJournal of the American Chemical Society, 1994
- Dependence of vicinal 31P–31P and 31P–13C coupling constants on the dihedral angle of α, β‐diphosphonatesMagnetic Resonance in Chemistry, 1990