ISSN:
0170-2041
Keywords:
Phosphorus ylides
;
Acyl dichlorides
;
Benzonitrile imine
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses with 1,3-Ambident-Nucleophilic Phosphorus Ylides, VII. - Heterocyclic Triphenylphosphonium Chlorides, Triphenylphosphonio-Olates, Acyclic Triphenylphosphonio-Thiolates and Their Wittig DerivativesUnder mild conditions, benzoylmethylenetriphenylphosphorane (1b) reacts readily with oxalyl chloride to give the unstable 4-(4,5-dihydro-4,5-dioxo-2-phenyl-3-furyl)triphenylphosphonium chloride (3b). This undergoes rapid hydrolysis to afford the triphenylphosphonium chloride 4 of benzoylpyruvic acid. Thermolysis of 3b or 4 results in the formation of 2-(triphenylphosphoranyliden)indan-1,3-dione (10), the structure of which was established by X-ray diffraction analysis. - With phenylmalonyl chloride, the title compounds 1a, b, d react by formation of the triphenylphosphonio-olates 7 of pyridine-, pyran- and thiopyran-dione, respectively. - The (thioaroylmethylene)triphenylphosphoranes 1e, f react with benzonitrile imine 12 to give the red hydrazonotriphenylphosphoniothiolates 16, the structures of which have been elucidated by an X-ray diffraction analysis. Under rigorous conditions, compounds 16 undergo an intramolecular Wittig-type reaction leading to pyrazoles 14.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199319930123
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