Synthesis, Characterization and Crystal Structures of (Z)-1-[2-(Triphenylstannyl)vinyl]-1-indanol, Its Ester and Phenylhalostannyl Derivatives

Abstract

Abstract: (Z)-1-[2-(Triphenylstannyl)vinyl]-1-indanol 1 was synthesized by the additive reaction of 1-ethynylindanol with triphenyltin hydride. Compound 1 was esterified by phthalic anhydride to yield monoester derivative 2. Compounds 3 and 4 were prepared by the reaction of the monoester 2 with dibutyltin oxide and triphenyltin hydroxide, respectively. The phenyl groups in compound 1 were substituted by ICl, Br₂ or I₂ to yield mono-and dihalide derivatives(5-10). Compounds 1-10 were characterized by elemental analysis, ¹HNMR and FT-IR spectroscopy. The crystal and molecular structures of compounds 1 and 6 were determined by single crystal X-ray diffraction analysis. The Sn atom in compound 1 exhibits a distorted trigonal bipyramidal structure due to a weak intramolecular interaction between Sn and the hydroxyl O atoms [0.277 8(8) nm], while the Sn atom in compound 6 adopts a trigonal bipyramidal geometry with a significant Sn1←O interaction [0.236 4(2) nm]. The Lewis acidities of the Sn atoms are in the following order: PhSnX₂L>Ph₂SnXL>Ph₃SnL.

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

CLC Number:

O621.42

TrendMD:

WU Jun-Zheng, WANG Ke-Liang, KANG Wan-Li, ZHU Dong-Sheng . Synthesis, Characterization and Crystal Structures of (Z)-1-[2-(Triphenylstannyl)vinyl]-1-indanol, Its Ester and Phenylhalostannyl Derivatives[J]. Chem. J. Chinese Universities, 2005, 26(8): 1399.

References

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