✦ LIBER ✦

Synthesis and Photochemical Behaviour of 2-Amino-1,3-Cyclohexadienes

✍ Scribed by Ralf Kilger; Paul Margaretha

Publisher: John Wiley and Sons
Year: 1983
Tongue: German
Weight: 271 KB
Volume: 66
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19830660302

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✦ Synopsis

Abstract

The reaction of the 4,4‐dialkylated 2‐cyclohexenones 1 or 2 with a twofold excess of a secondary amine 3 affords the 2‐amino‐1,3‐cyclohexadienes 4 and 5, respectively. Irradiation (λ ≧ 300 nm) of the morpholino derivative 4a yields a mixture of the isomeric 3‐morpholino‐6‐methyl‐1,3,5‐heptatrienes 6 and 7, while 5 gives only one corresponding product 8. The reaction of enone 1 with an equimolar amount of pyrrolidine (3c) affords the bis‐enamine 9 which is converted to the unsaturated diketone 10 by oxidative hydrolysis.

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