ISSN:
0009-2940
Keywords:
Nitrilium salts
;
Nitrile oxides
;
N-Hydroxycarboximidoyl chlorides
;
1,2,4-Oxadiazolium salts
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260118
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