By Julius Stieglitz
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Extra info for A Theory of Color Production II, Inorganic Compounds
Reproduced with permission from J. Organomet. , 332, 13 (1987) Br(CH,),Br Br(CH,),CI Br(CH,),Br Br(CH2)Pr Br(CH,),Br Br(CH,),Br Br(CH,),Br 46b 45 50 48 77 80 79 50' - 8W 43 21 20 19 - "Yields represent percent conversion. Y. 'Yield of cyclic ether P h , C y (CH,). \ A further examination of the scope of the reaction system PhLi/CO/RBr and its application to the synthesis of useful intermediates have been recently published by Nudelman and coworkers"'. The reactivity of dihalo-substituted alkanes has been examined and it was found that only one bromine atom becomes substituted giving the corresponding haloalkyldiphenylcarbinol in good yield (equation 58 and Table 11); the only by-product is benzoin.
Geometries of LiCHO isomers at various levels". Reprinted with permission from J . Am. Chem. , 109, 2556 (1987). 101 \ "Distances in angstroms, angles in degrees. bIntegratedelectron population on lithium and oxygen at 3-21 G*. 'Natural population on lithium and oxygen at 6-31 Go. 3),therefore, there appears to be a contribution from an alkoxycarbene resonance form, 17, in the formyl ligand. l). g. 73 electrons in HBeCHO) is the result of a n-bond polarization which indicates that the formyl anion in these complexes has significant alkoxy-carbene character.
This reaction may be easily extended to produce cyclic ethers in a one-pot synthesis. Thus, the reaction of phenyllithium and the dihalo-substituted alkane with carbon monoxide is carried out as described, but the reaction mixture is not quenched with water. Instead, the solvent is distilled off by heating at 60°C (equation 59). From the residue the cyclic ether can be isolated in good yields (Table 11). Optimum yields are obtained for n = 3-5; the yield of cyclic ether decreases when the length of the alkyl chain increases.
A Theory of Color Production II, Inorganic Compounds by Julius Stieglitz