150982-68-6Relevant articles and documents
Selective Transformation of Strychnine and 1,2-Disubstituted Benzenes by C–H Borylation
Itami, Kenichiro,Saito, Yutaro,Segawa, Yasutomo,Yamanoue, Kotono
supporting information, p. 985 - 993 (2020/04/10)
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Photochemical preparation of highly functionalized 1-indanones
Wessig, Pablo,Glombitza, Clemens,Mueller, Gunnar,Teubner, Janek
, p. 7582 - 7591 (2007/10/03)
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.
Protoberberines from Reissert compounds, II: A new synthesis of 8-methyldibenzo[a,g]quinolizidines
Reimann,Renz
, p. 253 - 258 (2007/10/02)
The Reissert compounds 16 are benzylated by 2-bromomethylacetophenone dioxolane 14 to give the dihydroisoquinolines 5. Treatment of 5 with KOH yields the 1-benzylisoquinolines 6 which spontaneously form the deoxygenated coralynes 4 in acidic solution. 4a