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Preparation of 3,4,5-Trisubstituted 1,2,4-Oxadiazolium Salts from Nitrilium Salts (1993)

Abu-;El-Halawa, Rajab ; Shrestha-;Dawadi, Prativa Bade ; Jochims, Johannes C.

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 126 (1993), S. 109-116

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Details

ISSN: 0009-2940

Schlagwort(e): Nitrilium salts ; Nitrile oxides ; N-Hydroxycarboximidoyl chlorides ; 1,2,4-Oxadiazolium salts ; Chemistry ; Inorganic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 1,3-Cycloadditions of stable nitrile oxides 2 to nitrilium salts 1 afford high yields of 3,4,5-trisubstituted 1,2,4-oxadiazolium salts 3. N-Hydroxycarboximidoyl chlorides 4 add to nitrilium salts 1 to give isolable [(chloroalkylidene)aminooxyalkylidene]ammonium salts 5. A thermal stereomutation around the C = N+ bond is observed. On heating neat or in solution most compounds 5 cyclize to oxadiazolium salts 3. In cases where decomposition of 5 is faster than cyclization O-silylated N-hydroxycarboximidoyl chlorides 7 are treated with nitrilium salts 1 to furnish oxadiazolium salts 3.

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/cber.19931260118

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