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Azimine. VI. 1-Alkoxycarbony 1-2,3-dialkyl- und -2,3-diaryl-azimine

✍ Scribed by Christian Leuenberger; Lienhard Hoesch; André S. Dreiding

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
769 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

Azimines VI: 1‐Alkoxycarbonyl‐2,3‐dialkyl‐ and ‐2,3‐diarylazimines

Alkoxycarbonyl‐nitrenes 2 – generated in situ by α‐elimination from N‐[(4‐nitrophenyl)‐sulfonyloxy]carbamates 4 – were reacted with six aliphatic and aromatic azo compounds to yield 1‐alkoxycarbonyl‐azimines 11 (R′ = Alkyl). Thus, (2Z)‐ or (2E)‐ 1 ‐alkoxycarbonyl‐2,3‐diisopropyl‐azimines (8 or 9) were obtained stereospecifically from (E)‐ or (Z)‐1,1′‐dimethylazoethane (5 or 6) and 1‐alkoxycarbonyl ‐2,3‐(cis‐1,3‐cyclopentylene)‐azimines (10) resulted from 2,3‐diazabicyclo[2.2.1]‐2‐heptene (7), always using both ethoxy‐ and methoxycarbonyl‐nitrene (2a and 2b). With 2a, (E)‐azobenzene (14) was converted only to a single stereoisomer of 1‐ethoxycarbonyl‐2,3‐diphenyl‐azimine (17) and both stereoisomers of azo(p‐toluene) (15 or 16) reacted to give the same stereoisomer of 1‐ethoxycarbonyl‐2,3‐di(p‐tolyl)‐azimine (18).

📜 SIMILAR VOLUMES

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**Azimines IV. Kinetics and Mechanism of the Thermal Stereoisomerization of 2,3‐Diaryl‐1‐phthalimido‐azimines^1^)** Mixtures of (1__E__, 2__Z__)‐ and (1__Z__, 2__E__)‐2‐phenyl‐1‐phthalimido‐3‐__p__‐tolyl‐azimine (**3a** and **3b**, resp.) and (1__E__, 2__Z__)‐ and (1__Z__, 2__E__)‐3‐phenyl‐1‐phthal

Azimine. V.. Untersuchungen zur stereois
Azimine. V.. Untersuchungen zur stereoisomerie an der N(2), N(3)-bindung von 2, 3-dialkyl-1-phthalimido-aziminen
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**Azimines. V. Investigation on the Stereoisomerism Around the N (2), N (3) Bond in 2, 3‐Dialkyl‐1‐phthalimido‐azimines** 2, 3‐(__cis__‐1, 3‐Cyclopentylene)‐1‐phthalimido‐azimine (**7**) and isomerically pure (2 __Z__)‐ and (2 __E__)‐2, 3‐diisopropyl‐1‐phthalimido‐azimine (**9a** and **9b**) were p