- DIELS-ALDER REACTIONS OF VINYLBICYCLOHEPTENES
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Efficient syntheses of 1,3-dimethyl-2-vinylbicyclohept-2-ene (1) and 2,2-ethylenedioxy-4,6-dimethyl-5-vinylbicyclohept-4-ene (2) are described.These dienes, which undergo Diels-Alder reactions with p-benzoquinones readily, may serve as versatile intermediates for terpenoid synthesis.
- Sakaino, Makoto,Meinwald, Jerrold
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- ONO-pincer ruthenium complex-bound norvaline for efficient catalytic oxidation of methoxybenzenes with hydrogen peroxide
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The enhanced catalytic activity of ruthenium complex-bound norvaline Boc-l-[Ru]Nva-OMe 1, in which the ONO-pincer ruthenium complex Ru(pydc)(terpy) 2 is tethered to the α-side chain of norvaline, has been demonstrated for the oxidation of methoxybenzenes to p-benzoquinones with a wide scope of substrates and unique chemoselectivity.
- Yoshida, Ryota,Isozaki, Katsuhiro,Yokoi, Tomoya,Yasuda, Nobuhiro,Sadakane, Koichiro,Iwamoto, Takahiro,Takaya, Hikaru,Nakamura, Masaharu
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supporting information
p. 7468 - 7479
(2016/08/16)
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- Oxidation of Some 2-Methoxyphenols with Chlorous Acid
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Oxidation of 3-ethoxy-4-hydroxy-, 4-hydroxy-3-methoxy-5-methyl-, 3-chloro-4-hydroxy-5-methoxy-, and 2-hydroxy-3-methoxybenzaldehyde with chlorous acid gives, by oxidative aromatic ring cleavage between the oxygen-bearing carbon atoms, derivatives of (2Z, 4Z)-2,4-hexadienedioic acid in low yields.Chlorous acid oxidation of 2-methoxyphenol and 3-hydroxy-4-methoxybenzaldehyde yields methoxy-1,4-benzoquinone and 5,5-dichloro-6,6-dihydroxy-2-methoxy-2-cyclohexene-1,4-dione, respectively.The hydrate as well as the corresponding methyl hemiacetal undergoes base-catalyzed ring contraction to a derivative of 1-hydroxy-4-oxo-2-cyclopentenecarboxylic acid.The kinetics of the ring contraction of the hydrate was investigated in aqueous solutions in the pH range 1.15-3.65, where the rearrangement appears to be subject to specific base catalysis.
- Jaroszewski, Jerzy W.
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p. 2013 - 2018
(2007/10/02)
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