547. The synthesis of thyroxine and related substances. Part VII. The preparation of diphenyl ethers from 2 : 6-di-iodophenols

REACTIONS OF THE IODOMETAMECONINES1

“…N-($-Nitro-4-carbometJtoxyphenyl)pyridinium toluene-p-sulfonate (XII). Pure 2-nitro-4carbomethoxyphenyl toluene-p-sulfonate (8 g.) w-as warmed on the water-bath with pyridine (20 cc.). The ester soon dissolved, and the quaternary compound begun to separate after about 20 min.…”

Agents Affecting Lipid Metabolism. XII. N,N'-Disubstituted Cyclohexane-1,4-bis(methylamines)1

“…Table I , '-Dibenzyl Derivatives of Cyclohexane-1,4-bis(methylamine)°R These compounds are mixtures of cis and trans isomers unless otherwise indicated and were prepared by method A (see Experimental) except for 33 which was prepared by method B, and 32 which was obtained by reducing 31 with Raney nickel in ethanol at atmospheric pressure and room temperature. 6 This compound is a 1,4-irons isomer. 6 This method was used for the synthesis of most of the compounds of Table I and for some of the compounds of Table II (see tables for exceptions).…”

“…15 " All spectra were obtained using KBr plates. 6 The presence of two carbonyl bands indicates a mixture of monomer and dimer in the solid state. On the basis of earlier work [see L. J. Bellamy, "The Infared Spectra of Complex Molecules," John Wiley and Sons, Inc., New York, N. Y., 1958; E. J. Hartwell, It.…”

Thyroxine Analogs

“…The reaction of pyridine with dinitrophenyl ethers of this type had been reported. 10 We had further noticed the instability of this compound even when left wet with pyridine at room temperature for two days. We therefore changed reagents with the thought that the methanesulfonyl chloride might permit a faster reaction under milder conditions which would spare the resultant ether.…”