Synlett 2004(10): 1847-1848  
DOI: 10.1055/s-2004-829562
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Di-n-butyltin Oxide (DBTO)

Qian Wan*
Laboratoire de Chimie Organique Multifonctionnelle, UMR8164, ICMMO, Bât 420, Université de Paris-Sud, Orsay 91400 France
e-Mail: wanqian@hotmail.com;
Further Information

Publication History

Publication Date:
15 July 2004 (online)

Introduction

Di-n-butyltin oxide (DBTO), with the composition Bu2SnO, is an amorphous, polymeric powder insoluble in nonreacting solvents. It has been widely used for the ­selective manipulation of hydroxyl groups and polyols. The largest application of DBTO in organic chemistry is in the generation and reactions of stannylenes from polyhydroxy compounds. The stannylene acetals may be prepared by refluxing equimolar mixtures of substrate and DBTO in benzene or toluene, with a Dean-Stark apparatus. [1] Recently, Simas has reported that the stannylene intermediate formation does not require removal of water. [2] The synthesis of di-n-butylstannylene is faster in methanol, but this solvent must be removed prior to addition of the electrophile. [3] Formation of these tin derivatives can be greatly accelerated by microwave irradiation. [4]

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