Cyclic Dienes. VI. Synthesis of Substituted 1,2-Dimethylenecyclohexanes^1,2

The Synthesis of Novel Isoindoline Nitroxides Bearing Water‐Solubilising Functionality

“…Oxidation of the methyl groups at a later stage of the synthesis should then afford the desired carboxylic acid groups. Hence, 4,5-dimethylphthalic anhydride (22) was prepared according to the literature by a Diels-Alder reaction of 2,3-dimethyl-1,3-butadiene and maleic anhydride, [33] followed by aromatisation using bromine [34] to give 22. Subsequent reaction of 22 with benzylamine gave 2-benzyl-5,6-dimethylphthalimide (23) in an excellent yield (91 %) (Scheme 6), which when treated with EtMgI in refluxing toluene afforded 2-benzyl-5,6-dimethyl-1,1,3,3-tetraethylisoindoline (24) in a moderate yield (50 %).…”

“…Triethylamine and pyridine were dried by storage with potassium hydroxide. Crystalline K 4 [Fe(CN) 6 ]·3H 2 O was ground to a fine powder and then dried at 80°C at 0.5 Torr for 10 h. 2-Benzyl-1,1,3,3-tetraethylisoindoline [36] (7), 2-benzyl-1,1,3,3-tetramethylisoindoline [37] (10), 4,5-dibromophthalic anhydride [30] (16), 4,5-dimethylphthalic anhydride [30,33,34] (22) and 5-bromo-1,1,3,3-tetramethylisoindoline [25] (43) were prepared using established literature procedures. All other reagents were purchased from commercial suppliers and used without further purification.…”

Conformational Effects and Hydrogen Bonding in 1,4-Diols

“…Compounds 41 and 43 were donated by Dr. J. Sicher, as were the carboxylic acid precursors for the cis examples, 40 and 42.16 Compound 55 was furnished by Dr. J. Meinwald; hydrogenation gave compound 54. Compounds 2, 33, 34, 37, 44, 45, 46, 50, and 51 were prepared by the catalytic hydrogenation of compounds 22,35,36,38,47, 48, 49, 52, and 53, respectively. The remaining compounds were prepared by reduction of appropriate precursors or by following literature methods.…”

Phase selectively soluble dendrimer-bound osmium complex: a highly effective and easily recyclable catalyst for olefin dihydroxylationElectronic supplementary information (ESI) available: synthesis details, characterization of the osmium complexes, dihydroxylation and recycling procedure. See http://www.rsc.org/suppdata/cc/b4/b401994f/

“…3c The synthesis of these two types of dendritic ligands is outlined in Scheme 2. The coupling of 3,4,5-tri(n-decan-1-yloxy)benzyl chloride (1) 12 with 4-aminopyridine (2) or 4,5-dimethyl-cis-D 4 -tetrahydrophthalyl alcohol (3) 13 was successfully carried out using NaH as the deprotonation reagent to afford the dendritic ligands L1 and L2 in moderate yields, respectively. Both ligands were purified by flash column chromatography and characterized by 1 H, 13 C NMR and high-resolution mass spectroscopy.…”