Photochemical rearrangement of an acyclic .beta.,.gamma.-unsaturated ketone to a conjugated cyclopropyl ketone. An oxa-di-.pi.-methane rearrangement

Dauben, William G.; Kellogg, Michael S.; Seeman, Jeffrey I.; Spitzer, Wayne A.

doi:10.1021/ja00709a076

Cited by 53 publications

(26 citation statements)

References 2 publications

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“…The corresponding transformation of the positional isomer 71 was more efficient. Only one product (73) was obtained in high yield. In this case intermediate 72 (vinyl-benzo bridging) was generated.…”

Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 99%

“…For example, the ODPM rearrangement product 112 was obtained in 93% yield on irradiation of compound 113 in the presence of acetophenone as sensitizer (Scheme 23). 73 The presence of the phenyl ring is expected to favor ODPM by stabilization of radical intermediates. Conformational constraints induced by substituentes at the central carbon additionally favor the transformation of these biradicals into cyclopropane rings.…”

Section: Basic Mechanistic Considerations and Odpm Photoisomerizationmentioning

confidence: 99%

See 1 more Smart Citation

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 99%

Section: Basic Mechanistic Considerations and Odpm Photoisomerizationmentioning

confidence: 99%

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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“…The synthesis of hindered 4-pyridones (1-5) utilized the condensation15 of the corresponding 4-pyrones (6)(7)(8) with alkylamines. The structure assigned O R.…”

Section: Resultsmentioning

confidence: 99%

Photoisomerization of 4-pyridones to 2-pyridones

Ishibe¹,

Masui²

1974

J. Am. Chem. Soc.

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“…The corresponding hydrocarbon (4)3 possessing an exomethylene group was obtained in 85 % yield by reaction of methylenetriphenylphosphorane with ketone (3) benzylic and the methylene groups as proposed in the structure shown (7). Although the sensitized photolysis of (4) in acetone also afforded photoisomer (7) (4) does not lead to the actual photoproduct (7) but to the isomer (7a) which could not be detected in the photolysis.…”

mentioning

confidence: 99%