1973
DOI: 10.1021/ja00793a020
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Photochemical ring expansion of cyclic aliphatic ketones. Cyclobutanones and cyclopentanones

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Cited by 46 publications
(13 citation statements)
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“…Different from the photodecomposition in the gas phase, the cyclobutanone in solution (alcohol) was found to undergo photochemical ring expansion to the cyclic acetal in addition to decarbonylation and cycloelimination reactions [15]. The transient intermediate was proposed as a cyclic oxacarbene (1A in Scheme 1) having the five-membered ring structure [16,17].…”
Section: Introductionmentioning
confidence: 99%
“…Different from the photodecomposition in the gas phase, the cyclobutanone in solution (alcohol) was found to undergo photochemical ring expansion to the cyclic acetal in addition to decarbonylation and cycloelimination reactions [15]. The transient intermediate was proposed as a cyclic oxacarbene (1A in Scheme 1) having the five-membered ring structure [16,17].…”
Section: Introductionmentioning
confidence: 99%
“…1,1,2,2-tetramethyl-3-methylenecyclopropane and 1,l-dimethyl-2-3There are some examples of 1,2-hydrogen shifts leading to en01 isopropylidenecyclopropane (19)) but these could not be isolated. For personal use only.…”
Section: Resultsmentioning
confidence: 99%
“…The photochemical reactions undergone by cyclic ketones have for some time been of widespread interest (2), the principal products being carboxylic acid derivatives (3), enals (2), and cyclic ethers (4,5). Acyl alkyl diradical intermediates (6,7) are commonly invoked and may arise from either the singlet or triplet excited states of the ketone (4,8,9).…”
mentioning
confidence: 99%
“…Acyl alkyl diradical intermediates (6,7) are commonly invoked and may arise from either the singlet or triplet excited states of the ketone (4,8,9).…”
mentioning
confidence: 99%