Photo-umlagerung von 2.4.6-triphenyl-o-chinolacetat

Perst, H.; Mitarbeit, Unter; Sprenger, William A.

doi:10.1016/s0040-4039(01)98538-7

Cited by 7 publications

(2 citation statements)

References 8 publications

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“…G.1.c. monitoring (column 1 at 183 "C) of a smaller scale irradiation under the above conditions showed that after 15 min (and 22 min) compounds ( 13), ( 14), ( 15), (16), and (17) were present in yields of 32 (lo), 30 (42), 16 (24), and 2% (4%) respectively.…”

Section: Irradiation Of' 2-aceto~y-2-rnethylnaphthalen-1 (2h)-one (4)...mentioning

confidence: 91%

“…analysis (column 1 at 183 and 225 "C). After 30 min (and 60 min) irradiation compounds (13), ( 14), ( 15), (la), and (17) were present in yields of < 1 (< l), 27 (16), 55 (31), 10 (17), and 1% (3%) respectively. 2-Acetoxy-1,l -dimethyl-1,2-dihydronaphthalene (12).-A solution of l,l-dimethylnaphthalen-2(lH)-one 2 3 (5.9 g) in dry ether (30 ml) was added with stirring to a suspension of lithium aluminium hydride (2.64 g) in dry ether, and the mixture was stirred at room temperature for 5 min.…”

Section: Irradiation Of' 2-aceto~y-2-rnethylnaphthalen-1 (2h)-one (4)...mentioning

confidence: 99%

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The photochemistry of 2-acetoxynaphthalen-1(2H)-ones

Greenland¹,

Pinhey²,

Sternhell³

1986

J. Chem. Soc., Perkin Trans. 1

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Section: Irradiation Of' 2-aceto~y-2-rnethylnaphthalen-1 (2h)-one (4)...mentioning

confidence: 91%

Section: Irradiation Of' 2-aceto~y-2-rnethylnaphthalen-1 (2h)-one (4)...mentioning

confidence: 99%

The photochemistry of 2-acetoxynaphthalen-1(2H)-ones

Greenland¹,

Pinhey²,

Sternhell³

1986

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: PHOTOUMLAGERUNG VON 2,4,6‐TRIPHENYL‐O‐CHINOLACETAT

Perst¹

1970

Chemischer Informationsdienst. Organische Chemie

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Über Dienketene aus o‐Chinolacetaten

Quinkert

Kleiner

Freitag

et al. 1986

Helvetica Chimica Acta

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(RS)- 6-acetoxl.-5,.6-dimeth?.l-, (RS)-6-ucetoxy-2,4,6-1rimeth~.l-, 3,4,6-tet r m n i 4 i j~l -. and (RS)- 6-oci~tox~-2,3,4,5,6-pentumeth~l-2,4-c~clo/ie.~udii~n-I-oni~.~ serve as representative educts.Thcrc arc two separate main photochemical routes conveniently designated as l(n*, n) or '(n*, n ) tracks. The latter may also he attained by sensitization and leads to phenols. The former, by a-cleavage furnishes dien-ketens as indispensable phototransients. Photolysis of dien-ketens follows one or more of three reaction channels, each of which yields a particular type of photoproduct: heat-induced monocyclization affords 2,4-cyclohexadien-1-ones, heat-induced hicyclization stereoselectively furnishes bicyclo[3.1.0]hex-3-en-2-ones, and multi-step addition of protic nucleophiles stereosclcctively gives l,4-, I,6-and/or 1,2-adducts. By X-ray analysis or NOE studies, the structure of isolated photoproducts is establishcd. Conventional spectroscopy at low or flash spectroscopy at normal temperature yield information on the Cormation and decay of kinetically unstable intermediates. Photoproduct composition depends on the pattern o C substitution of the educts, o n thc solvents, and on the nucleophiles that might he present. Substituents primarily exert an influence upon the population of the various conformers of the dien-ketcn. Solvents affect the rate of the divers reaction paths competing for the phototransient. Nucleophiles play more than a trivial role when adducts are formed. With the detailed view of a dien-keten's role on hand, the photoproduct from a given o-quinol-acetate -or more general from a linear conjugatcd cyclohexadienone -is now predictable.

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Photo-umlagerung von 2.4.6-triphenyl-o-chinolacetat

Cited by 7 publications

References 8 publications

The photochemistry of 2-acetoxynaphthalen-1(2H)-ones

The photochemistry of 2-acetoxynaphthalen-1(2H)-ones

ChemInform Abstract: PHOTOUMLAGERUNG VON 2,4,6‐TRIPHENYL‐O‐CHINOLACETAT

Über Dienketene aus o‐Chinolacetaten

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