2007
DOI: 10.1016/j.tet.2007.08.054
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Synthesis of bicyclo[3.2.1]octanones via ketyl radical promoted rearrangements under reductive PET conditions

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Cited by 13 publications
(11 citation statements)
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“…Finally, the suitability of the organogel for applications as a micro-reactor was tested by carrying out the photochemical reaction of 3 (Scheme 2). 16 Organogels from D-/L-1 are ideal for photochemical reactions due to the lack of any light absorbing chromophore in the gelator itself. A mixture of 3 and D-/L-1 in benzene was warmed and subsequently allowed to cool to room temperature, when a gel was formed.…”
mentioning
confidence: 99%
“…Finally, the suitability of the organogel for applications as a micro-reactor was tested by carrying out the photochemical reaction of 3 (Scheme 2). 16 Organogels from D-/L-1 are ideal for photochemical reactions due to the lack of any light absorbing chromophore in the gelator itself. A mixture of 3 and D-/L-1 in benzene was warmed and subsequently allowed to cool to room temperature, when a gel was formed.…”
mentioning
confidence: 99%
“…In order to investigate the photoreaction of such enones, we observed a complete 1,2-acyl shift (1,2-AS) photoproduct formation when 1a-h have been irradiated (Scheme 1) [14,16]. We also observed that such a rearrangement took place very efficiently via a triplet-mediated pathway without use of any external sensitizer.…”
Section: Formation Of An Exceptionally Stable Ketene During Phototranmentioning
confidence: 91%
“…For several years, our laboratory (S. Lahiri et al) is primarily engaged in synthesizing various types of such multichromophoric systems to compare their photochemistry in detail [9][10][11][12][13][14][15]. Since in acyclic enones like C, E/Z-photoisomerization becomes one of the major energy dissipation pathways, we selected rigid bicyclic multichromophoric enones like D to minimize this route.…”
Section: Formation Of An Exceptionally Stable Ketene During Phototranmentioning
confidence: 99%
“…After 1 h of irradiation, the analysis of the mixtures showed similar yield (88%) and kinetics to those obtained in solution. Furthermore, the gelator was also recovered from the mixture after column chromatography …”
Section: Photodimerizationmentioning
confidence: 99%