Isoindoline N-oxides

In an approach developed by Kreher and Seubert,30 the isoindoline N-oxides undergo an analogous elimination when treated with an acylating... 

Acetic anhydride-triethylamine Isoindoles from isoindoline N-oxides s. 20, 648a suppl. 29... 

Elimination from N-oxides of substituted isoindolines provides an exceptionally facile synthesis of the isoindole system. Kreher and Seubert found that treatment of the oxides of both 2-alkyl-28 and 2-arylisoindolines24 with acetic anhydride at 0° to —10° afforded... 

In the presence of trace amounts of water, the tetrameric p,2-oxo complex (182) in 1,2-dimethoxyethane is transformed into a p, -oxo tetrameric complex (183 equation 254), characterized by an X-ray structure.574 In contrast, (182) 572,575 is inactive towards the oxidation of phenols. The reaction of N,N,N, AT -tetramethyl-l,3-propanediamine (TMP) with CuCl, C02 and dioxygen results in the quantitative formation of the /z-carbonato complex (184 equation 255).s76 This compound acts as an initiator for the oxidative coupling of phenols by 02. 6 Such jz-carbonato complexes, also prepared from the reaction of Cu(BPI)CO with 02 [BPI = 1,3 bis(2-(4-methyl-pyridyl)imino)isoindoline],577 are presumably involved as reactive intermediates in the oxidative carbonylation of methanol to dimethyl carbonate (see below).578 Upon reaction with methanol, the tetrameric complex (182 L = Py X = Cl) produces the bis(/z-methoxo) complex (185 equation 256), which has been characterized by an X-ray structure,579 and is reactive for the oxidatiye cleavage of pyrocatechol to muconic acid derivatives.580,581... 

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