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Media type:
E-Article
Title:
Neue Azoolefine und deren saure Spaltung zu Aryldiiminen
Contributor:
Kirschke, Klaus;
Möller, Angela;
Schmitz, Ernst
imprint:
Wiley, 1985
Published in:Journal für Praktische Chemie
Language:
English
DOI:
10.1002/prac.19853270604
ISSN:
0021-8383
Origination:
Footnote:
Description:
<jats:p><jats:bold>New Azoolefines and their Acidic cleavage to Aryldiimines</jats:bold></jats:p><jats:p>3‐Amino‐1‐aryl‐3′,3′‐dimethyl‐pyrazolin‐4‐spiro‐2′‐oxiran‐5‐ones (<jats:bold>3a</jats:bold>–<jats:bold>c</jats:bold>) undergo ring opening with methoxide forming methyl 3‐amino‐3‐arylazo‐propenoates (<jats:bold>5a</jats:bold>–<jats:bold>c</jats:bold>). <jats:bold>5a</jats:bold>–<jats:bold>c</jats:bold> are cleaved under acidic conditions. The main products of the cleavage of <jats:bold>5c</jats:bold> with methanolic hydrochloric acid are nitrogen, 2, 4, 6‐trichloro‐benzen (<jats:bold>6</jats:bold>), 2, 4, 6‐trichloro‐aniline (<jats:bold>9</jats:bold>) and 2, 4, 6‐trichlorophenylhydrazine (<jats:bold>10</jats:bold>). Intermediates of the cleavage of 5 are aryldiimines trapped with benzaldehyde as the corresponding benzhydrazides (<jats:bold>12a</jats:bold>, <jats:bold>b</jats:bold>).</jats:p>