Kinetic evidence for remote π-aryl participation in the BF 3-catalyzed rearrangement of [2 + 2] photocycloadducts of diarylhomobenzoquinones with diphenylacetylene

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4081-4084

  Koizumi, Takuya ^a   Harada, Kenji ^a   Mochizuki, Eiko ^a   Kokubo, Ken ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; KINETICS; PHOTOCHEMISTRY; STEREOCHEMISTRY; SUBSTITUTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 8744262981     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0481986     Document Type: Article

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21. 2 (0.06 mmol), and the solution was allowed to stand for 70 h at 25°C to give quantitatively 3f. The pure 3f was obtained after washing with water (2 x 1 mL) and then recrystallization from benzene-pentane.
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33. 31P NMR chemical shifts of triethylphosphine oxide. The acidity of chloroform (AN = 23.1) is stronger than 1,2-dichloroethane (16.7) and dichloromethane (20.4), being related to the hydrogen bonding interaction with the oxygen atom. See: (a) Gutmann, V. Electrochem. Acta 1976, 21, 661. (b) Parker, A. J.; Mayer, U.; Schmid, R.; Gutmann, V. J. Org. Chem. 1978, 43, 1843.