Triplet photosensitization of 2-norbornenone and other β,γ-unsaturated ketones
✍ Scribed by Mary A. Schexnayder; Paul S. Engel
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 227 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The diversity of photochemical reactions exhibited by 0,y-unsaturated ketones' (g,y-UK's) has prompted us to examine the triplet state properties of soms representative compounds.
The follow ing conclusions have emerged from this study 1) 2-norbornenone (lJ undergoes an unusual triplet sensitized 1,3-acyl shift.
- The previously reported2 phosphorescence data for 1 and 2 are erroneous. 3) Formation of an excited complex accounts for much of the interaction between S,Y-UK's and aromatic ketone triplet sensitizers.
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Quantum yields for ketone disappearance and for product appearance in the triplet sensitized irradiation of compounds 1-3 are shown in Table I. __ Contrary to the usual behavior of 6,y-UK's,l triplet _l_ gives a considerable amount of the 1.3~acyl shift product 4' in addition to the repor-ted4 oxadivnlllethane product 2. Although one is tempted to attribute this result to singlet sen-
📜 SIMILAR VOLUMES
The photochemistry of b,g-unsaturated ketones has been a topic of great interest to organic photochemists for many years. [1] The results of studies in this area show that these substances undergo a 1,3-acyl migration on direct irradiation and an oxa-di-p-methane (ODPM) rearrangement in the presence
The photochemistry of b,g-unsaturated ketones has been a topic of great interest to organic photochemists for many years. [1] The results of studies in this area show that these substances undergo a 1,3-acyl migration on direct irradiation and an oxa-di-p-methane (ODPM) rearrangement in the presence
## Abstract For Abstract see ChemInform Abstract in Full Text.
We recently reported the singlet-state photochemical rearrangement of 3-methylene-2,2,5,5-tetramet~lcyclohexanone (1) via a 1,3-sigmatropic acyl shift to 3,3-dimethyl-5-isopropylidenecyclohexanone (g).", However, 17~-acetoyy-4,4-dimetQrl-19-norandrost-5-en-3-one (3)isknown to undergo a triplet-state