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Photodimerization of N-acetyl-2-azetine: Synthesis of syn-diazatricyclooctane and anti-diazatricyclooctane (diaza-3-ladderane)

✍ Scribed by Paritosh R Dave; Rajagopal Duddu; Jianchang Li; Rao Surapaneni; Richard Gilardi


Book ID
104259595
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
178 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis


Photodimerization of N-acetyl-2-azetine to yield both possible head to head dimers with syn and anti geometries is described.


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Both syn-and anri-[2.n](3,9)carbazolophanes (n = 4, 5) were obtained by the intramolecular [2 + 21 photocycloaddition of bis(3-vinyl-N-carbazolyl)alkanes. In the case of R = 4, the syn-isomer afforded sandwich excimer fluorescence, whereas the antiisomer Rave monomer fluorescence.