+++Roczniki Chemii

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Janczewski,M.; Dziurzynska,B.; Roczniki Chemii; vol.48; (1974); p. 409 - 430

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Effect of molecular structure on optical properties on sulfoxide systems. LV-​LVI. Optical relations in the 4-​diphenylsulfinylacetic acids group and in their 4'-​ethyl- and 4'-​tert-​butyl derivatives
By Janczewski, Marian; Dziurzynska, Bozenna
From Roczniki Chemii (1974), 48(3), 409-31. | Language: English, Database: CAPLUS
Sulfinylacetic acids (I, R = Et and Me3C) were prepd. as model compds. for studying the inductive and hyperconjugation effects of the alkyl group on rotation of the optical isomers. Thus, sulfonation of 4-RC6-H4Ph gave II, which was converted to III. Subsequent redn. with SnCl2 yielded IV, which, treated in alk. medium with ClCH2CO2H, gave V. Oxidn. of V with H2O2-AcOH gave I. III (R = Et) was also prepd. in low yield by direct chlorosulfonation of 4-EtC6H4Ph. III (R = Et) was reduced with Na2SO3 to VI (R = Et), which was converted to 4-EtC6H4C6H4I-4, identical with a sample prepd. by N2H4 redn. of 4-MeCOC6H4C6H4I-4. The sulfonamide, S-benzyl deriv. of IV, and Me ester of V were reported in the R-Et and Me3C series; moreover, benzylsulfonyl analog of VI (R = Et), S-(2,4-dichlorophenyl) deriv. of IV (R = Et) and S-(2,4-dinitrophenyl) deriv. of IV (R = Me3C) were prepd. The (+)- and (-)-isomers of I (R = Et) and (+)-and (-)-I (R = Me3C) were obtained via the morphine, hydrocinchonidine, cinchonidine, and cinchonine salts, resp. Me, 4-O2NC6H4CH2, and 4-BrC6H4COCH2 esters and amides of the two racemic I and (-)-I were prepd. by routine procedures. Both I were also oxidized with H2O2-AcOH to the corresponding sulfones. ORD, CD, and uv measurements revealed that the rotation values were greatly affected by the solvent and that in the visible part of the spectrum the rotatory dispersion had a normal character. The alkyl substituent in I increased the rotation, this increase being smaller for the tertiary alkyl. Rotation due to the sulfoxide chirality center seemed also to be affected by hyperconjugation of the alkyl group in a quinoid-like system.

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