On the regioselectivity of metal hydride reductions of 3-substituted phthalic anhydrides
A problem of 3-methoxyphthalide reduction by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qualitative interpretation of the results is now proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.
Soucy,Favreau,Kayser
p. 129 - 134
(2007/10/02)
17O NUCLEAR MAGNETIC RESONANCE SPECTROSCOPIC STUDY OF SUBSTITUTED PHTHALIC ANHYDRIDES AND PHTHALIDES
17O chemical shift data (natural abundance) for 3-substituted phthalic anhydrides and 4- and 7-substituted phthalides in acetonitrile at 75 deg C are reported.Steric interactions of substituents ortho to the carbonyl groups result in deshielding effects (9-22 ppm) relative to parent compounds regardless of the electronic character of the substituents.Factors contributing to the deshielding effects are discussed.The relationship between 17O chemical shifts and regiochemistry of the phthalic anhydrides is discussed.
Boykin, David W.,Baumstark, Alfons L.,Kayser, Margaret M.,Soucy, Chantal M.
p. 1214 - 1217
(2007/10/02)
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