Preparation and Addition of 3-Bromo-2-oxotetrahydro-1,3-oxazoles to Styrene and Derivatives Some New Tetramisole Intermediates

Dockx, Jozef; Knaep, Alfons G. M. De; ALBERT, R. W. H.

doi:10.1055/s-1982-29862

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1982

2012

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Mild and High‐Yielding Molybdenum(VI) Dichloride Dioxide‐Catalyzed Formation of Mono‐, Di‐, Tri‐, and Tetracarbamates from Alcohols and Aromatic or Aliphatic Isocyanates

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Brückner

2012

Adv Synth Catal

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Both molybdenum(V) dichloride dioxide (MoO 2 Cl 2 ) and its dimethylformamide (DMF) complex catalyze the addition of alcohols to isocyanates giving carbamates. Most additions proceed to completion at room temperature within 20 min using as little as 0.1 mol% of the catalyst when working on a 1-mmol scale or just 100 ppm working on a 20-mmol scale. Sterically encumbered substrates reacted to completion when 1 mol% of the catalyst was employed. Diols, triols, and tetraols reacted with monoisocyanates likewise, as did monofunctional alcohols and diisocyanates. These pairings furnished di-, tri-, tetra-, and dicarbamates, respectively. Reactants, which were poorly soluble in CH 2 Cl 2 at room temperature required elevating the temperature and possibly choosing a higher-boiling solvent (ClCH 2 CH 2 Cl, DMF) as well. Additions of diols to diisocyanates were feasible, too, giving polycarbamates as we presume.

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