Isolation of Cyclohexadienone Intermediates in the Photo-Fries Rearrangement of 2,4-Dimethylnaphth-1-yl and 1,4-Dimethylnaphth-2-yl 2,4,6-Trimethylbenzoates

Isolation of Cyclohexadienone Intermediates in the Photo-Fries Rearrangement of 2,4-Dimethylnaphth-1-yl and 1,4-Dimethylnaphth-2-yl 2,4,6-Trimethylbenzoates

Labile cyclohexadienones were isolated for the first time in good yields in the photo-Fries rearrangement of partially blocked naphthyl esters. Upon direct excitation at 313 nm, 1,4-dimethylnaphth-2-yl and 2,4-dimethylnaphth-1-yl 2,4,6-trimethylbenzoates afforded 1-acyl-2-naphthalenone and 2- and 4-...

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Veröffentlicht in:Chemistry letters 2004-03, Vol.33 (3), p.254-255
Hauptverfasser: Mori, Tadashi, Takamoto, Makoto, Saito, Hideaki, Furo, Takahiro, Wada, Takehiko, Inoue, Yoshihisa
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container_end_page 255
container_issue 3
container_start_page 254
container_title Chemistry letters
container_volume 33
creator Mori, Tadashi
Takamoto, Makoto
Saito, Hideaki
Furo, Takahiro
Wada, Takehiko
Inoue, Yoshihisa
description Labile cyclohexadienones were isolated for the first time in good yields in the photo-Fries rearrangement of partially blocked naphthyl esters. Upon direct excitation at 313 nm, 1,4-dimethylnaphth-2-yl and 2,4-dimethylnaphth-1-yl 2,4,6-trimethylbenzoates afforded 1-acyl-2-naphthalenone and 2- and 4-acyl-1-naphthalenones, respectively. This isolation is of particular importance as a direct mechanistic proof and also as a convenient route to these thermally less-accessible compounds.
doi_str_mv 10.1246/cl.2004.254
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title Isolation of Cyclohexadienone Intermediates in the Photo-Fries Rearrangement of 2,4-Dimethylnaphth-1-yl and 1,4-Dimethylnaphth-2-yl 2,4,6-Trimethylbenzoates
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