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Highly efficient photoinduced rearrangement of benzobicyclo[3.1.0]hexenones to 1-naphthols

✍ Scribed by Dong Jo Chang; Bong Ser Park

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
66 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Irradiation of 1-(o-tolyl)-3,4-benzobicyclo[3.1.0]hexenones (1) in benzene at 365 nm has resulted in clean conversion to 3-(o-tolyl)-1-naphthols (2) via 3-(o-tolyl)-1(2H)-naphthalenones. The reaction is suggested to occur mainly from (n, p*) 3 state with a reaction rate higher than 10 10 s -1 .

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UV Irradiation of 3-oxocyclopent-1-enyl acetate (17) and acetylene in MeCN at 0" gives, besides the product of normal enone-alkyne [2 + 21 cycloaddition (cis-4-oxobicyclo[3.2.0]hept-6-en-l-yl acetate, 18) and its product of oxd-di-n methane rearrangement (5-oxotricyclo[4.1 .0.02.']hept-2-yl acetate,