4709-20-0Relevant academic research and scientific papers
Copper-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadienes with Grignard and aluminum reagents
Millet, Renauds,Gremaud, Ludovic,Bernardez, Tania,Palais, Laetitia,Alexakis, Alexandre
experimental part, p. 2101 - 2112 (2009/12/31)
A highly enantioselective method for the copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand has been developed. The same reaction with Grignard reagents is also reported. A wide range of alky
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
Mori, Tadashi,Takamoto, Makoto,Saito, Hideaki,Furo, Takahiro,Wada, Takehiko,Inoue, Yoshihisa
, p. 254 - 255 (2007/10/03)
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.
Remarkable differences in photo and thermal (acid-catalyzed) reactivities between ortho-and para-acylcyclohexadienones as essential factors determining the overall efficiency of the photo-fries rearrangement
Mori, Tadashi,Takamoto, Makoto,Saito, Hideaki,Furo, Takahiro,Wada, Takehiko,Inoue, Yoshihisa
, p. 256 - 257 (2007/10/03)
Successful isolation of ortho and para - acylcyclohexadienones allowed us to comparatively study their ground- and excited-state behavior under a variety of conditions. In neutral solutions, the two isomeric cyclohexdienones showed completely different reactivities for photochemical and thermal reactions, while in acidic methanol both quantitatively afforded the corresponding transesterification product and naphthol. These studies help us understand the detailed photo-Fries rearrangement mechanism, which involves several crucial photochemical and thermal steps.
