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Photochemistry of 2-Cyclohexene-imines and 2,3,4,4a,5,6-Hexahydroquinolines. Preliminary communication

✍ Scribed by Paul Margaretha

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
360 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The 2‐cyclohexene‐imines 2b–2d and the hexahydroquinolines 5a, b are synthesized. n,π*‐Excitation of these α,β‐unsaturated imines leads to (E/Z) isomerization for compounds 2 while compounds 5 are unreactive. No cyclobutanes are formed from 2 or 5 under these conditions in the presence of olefins, and only 2d adds to 2,3‐dimethyl‐2‐butene via the CN bond to give an azetidine. On π,π* excitation 2 and 5 rearrange to the corresponding β,γ‐unsaturated imines 8 and 9 with low efficiency. It is concluded that the failure of such imines to undergo [2+2]‐photocycloadditions with olefins is not mainly due to radiationless decay via (E/Z) isomerization.

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