Synthesis and Characterization of (Z)‐1‐[2‐(Tribenzylstannyl)vinyl]‐1‐cycloheptanol and its Benzylhalostannyl Derivatives

Abstract

1‐Ethynyl‐1‐cycloheptanol reacts with tribenzylstannylhydride, (C₆H₅CH₂)₃SnH, and generates the corresponding (Z)‐1‐[2‐(tribenzylstannyl)vinyl]‐1‐cycloheptanol. The product obtained reacts with one or two equivalents of halogen (I₂, Br₂ or ICl) to form the associated (Z)‐1‐[2‐(dibenzylhalostannyl)vinyl]‐1‐cycloheptanol or (Z)‐1‐[2‐(benzyldihalostannyl)‐vinyl]‐1‐cycloheptanol, respectively. All compounds were characterized by elemental analyses, IR, ¹H NMR. The X‐ray diffraction analysis of (Z)‐1‐[2‐(tribenzylstannyl)vinyl]‐1‐cycloheptanol shows the presence of an intramolecular coordination of oxygen to the tin atom giving rise to a five‐membered ring in which the metal exhibits a distorted trigonal‐bipyramidal geometry. This may explain that a benzyl group, probably the apical one, is cleaved more easily by halogen than the vinyl substituent.

Keywords:

• Synthesis
• Characterization
• Organotin compound

Acknowledgments

This project was supported by the Dalian University of Technology Innovate Foundation.