cas 6742-25-2, Ethyl 1-Oxo-2,3-Dihydro-1H-Indene-2-Carboxylate | Articles data ｜lookchem

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6742-25-2

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Photochemical preparation of highly functionalized 1-indanones
A series of o-alkylphenyl alkyl ketones 1 were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-π* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo-[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.
Wessig, Pablo,Glombitza, Clemens,Mueller, Gunnar,Teubner, Janek
p. 7582 - 7591
(2007/10/03)

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Chemical Properties

Melting Point: 144-145 °C
Boiling Point: 185 °C(Press: 20 Torr)
Density: 1?+-.0.06 g/cm3(Predicted)
PKA: 10.36±0.20(Predicted)
PSA: 43.37000
LogP: 1.60470

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