Synthesis, Characterization and Crystal Structure of (Z)-1-Triphenylstannyl-3-p-chlorophenyl-1-butene-3-ol and Their Arylhalostannyl Derivatives

Abstract

Abstract: (Z)-1-Triphenylstannyl-3-p-chlorophenyl-1-butene-3-ol(1) was synthesized by the additive reaction of 3-p-chlorophenyl-1-butyne-3-ol with triphenyltin hydride. The phenyl groups in compound 1 were substituted by ICl, Br₂ or I₂ to yield mono- and dihalide derivatives(2—8). Compounds 1—8 were characterized by elemental analysis, ¹H NMR and FTIR spectroscopy. The crystal structures of compounds 1, 3 and 5 were determined by single crystal X-ray diffraction analysis. Sn atom in compound 1 exhibits a distorted tetrahedral structure due to a weak intramolecular interaction between Sn and the hydroxyl O atoms (0.281 and 0.283 nm), while the Sn atom in 3 and 5 adopts a trigonal bipyramidal geometry with a significant Sn1←O interaction [0.240 1(6) nm in 3 and 0.238 4(7) nm in 5]. The Lewis acidities of the Sn atoms are in the following order: PhSnX₂>Ph₂SnX>Ph₃Sn.

Key words: Organotin(Ⅳ), Syntheses, Characterization, Crystal structure

CLC Number:

O621.42

TrendMD:

ZHU Dong-Sheng, LI Xing-Qi, MEI Ze-Min, L� Chun-Sheng, MU Ying. Synthesis, Characterization and Crystal Structure of (Z)-1-Triphenylstannyl-3-p-chlorophenyl-1-butene-3-ol and Their Arylhalostannyl Derivatives[J]. Chem. J. Chinese Universities, 2004, 25(4): 641.

References

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