Photochemical reactions. 137th communication. Preparation and photolysis of (E/Z)??7??methyl?螃漫?ionone

K Ishii, P Mathies, T Nishio, HR Wolf…

Index: Ishii, Keitaro; Mathies, Peter; Nishio, Takehiko; Wolf, Hans Richard; Frei, Bruno; Jeger, Oskar Helvetica Chimica Acta, 1984 , vol. 67, p. 1175 - 1183

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Citation Number: 9

Abstract

Abstract The title compounds (E/Z)-7 were prepared in 66% overall yield by reaction of β- ionone ((E)-(1) with lithium dimethylcuprate, trapping of the intermediate enolate with benzeneselenenyl bromide and oxidation with H 2 O 2. Analogously,(E/Z)-7-methyl-α-inone ((E/Z)-12) was obtained in 65% yield from α-ionone ((E)-11). 1 n, π*-Excitation (λ> 347 nm, pentane) of (E)-7 causes rapid (E/Z)-isomerization and subsequent reaction of (Z)-7 to 15 ( ...