1997
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Abstract: The cyclopropylmethyl and (trans-2-phenylcyclopropyl)methyl radical clocks were used to estimate the lifetimes of triplet state biradicals formed from substituted 1-alkoxy-9,10-anthraquinones by photoexcitation and subsequent 1,5-hydrogen atom transfer. Irradiation (350 nm) of 1-(cyclopropylmethoxy)-2-methyl-9,10-anthraquinone (1cp) in argon-purged methanol generated the primary anthrahydroquinone product (2). Upon exposure to air, 2 was rapidly converted to cyclopropanecarboxaldehyde and 1-hydroxy-2-X-9,10-an… Show more

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“…Therefore, these results are in agreement with rapidly rearranging 1,5 biradicals. 8 On the other hand, taking into account literature reports on benzophenone-bridge-norbornediene triads systems where intramolecular energy transfer from the n,p* carbonyl triplet initiates the photoisomerization process, 31 we likewise postulate an intramolecular energy transfer from the benzophenone triplet to the side-chain (Scheme 4) in the case of compound 2.…”
Section: Proposed Mechanism Pathwaysmentioning
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“…Therefore, these results are in agreement with rapidly rearranging 1,5 biradicals. 8 On the other hand, taking into account literature reports on benzophenone-bridge-norbornediene triads systems where intramolecular energy transfer from the n,p* carbonyl triplet initiates the photoisomerization process, 31 we likewise postulate an intramolecular energy transfer from the benzophenone triplet to the side-chain (Scheme 4) in the case of compound 2.…”
Section: Proposed Mechanism Pathwaysmentioning
“…Dimesitylbis(trimethylsilyl)silane and hexamesitylsiladigermirane were prepared following the reported procedures. trans -(2-Phenylcyclopropyl)carboxylic acid was reduced with lithium aluminum hydride in diethyl ether to give the corresponding alcohol which was subsequently oxidized using Swern conditions to trans -(2-phenylcyclopropyl)carboxaldehyde …”
Section: Methodsmentioning
“…This compound also undergoes intramolecular d H-abstraction which further leads to the oxidative cleavage of the 1-alkoxy group as an aldehyde (Blankespoor et al, 1991(Blankespoor et al, , 1995(Blankespoor et al, , 2002Smart et al, 1997). In this photoreaction, five types of photoproducts 109-113 are obtained (Scheme 27).…”
Section: Synthesis Of 1-hydroxy-910-anthraquinonesmentioning