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Photochemistry of N-(2-Cyclohexen-1-ylidene) alkylamines

✍ Scribed by Ralf Kilger; Pual Margaretha

Publisher: John Wiley and Sons
Year: 1984
Tongue: German
Weight: 300 KB
Volume: 67
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19840670315

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✦ Synopsis

Abstract

Irradiation (λ = 254 nm) of N‐(4,4,6,6‐tetramethyl‐2‐cyclohexen‐1‐ylidene)‐1,1,3,3‐tetramethyl‐2‐cyclohexen‐1‐ylidene‐1,1,3,3‐tetramethylbutylamine (7d), which in turn is photodecomposed by light of the same wavelength, but at a four times slower rate than it is formed. The rate of formation of photoproduct 7d is a function of the concentration of starting material 1d, suggesting the involvement of a bimolecular (1d^*^ + 1d) step. The structure of 7d was established by spectroscopy and by its hydrolysis to 3‐cyclohexyl‐4,4,6,6‐tetramethyl‐2‐cyclohexenone (8). The previously made assumption that N‐(2‐cyclohexen‐1‐ylidene)cyclohexylamine (1a) and 2,3,4,4a,5,6‐hexahydroquinolines 2 photorearrange to N‐cyclohexylidenecyclohexanamine 3a and 3,4,4a,5,6,8a‐hexahydroquinolines 4, respectively, via a light‐induced 1,3‐hydrogen shift proves incorrect.

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