Oligomerization of vinyl monomers. 17. Stereoselective methylation of 1-lithio-1, 3-bis (phenylsulfinyl) butane. Kinetic vs. thermodynamic control in the formation of …

MA Buese, TE Hogen-Esch

Index: Buese, Mark A.; Hogen-Esch, Thieo E. Journal of the American Chemical Society, 1985 , vol. 107, # 15 p. 4509 - 4513

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Citation Number: 14

Abstract

Abstract: The addition of (R)-or (R, S)-vinyl phenyl sulfoxide (3) to (R)-or (R, S)-1-lithio-1- (phenylsulfiny1) ethane (2) was carried out in THF at-78 OC, and the adduct anion 4 was protonated or methylated to produce 1, 3-bis (phenylsulfinyl) butane (6) or 2, 4-bis (phenylsulfinyl) pentane (5). The stereochemistry of methylation was shown to strongly depend upon the 3/2 ratio and the method of preparation of Li-4, including its thermal ...