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5.2.9 Product Subclass 9: Tin Oxides

DOI: 10.1055/sos-SD-005-00300

Jousseaume, B.Science of Synthesis, (20035353.

General Introduction

Previously published information regarding this product subclass can be found in HoubenWeyl, Vol. 13/6, pp 300310. Reviews on the synthesis and chemical properties[‌1‌] as well as on the applications of organotin oxides and alkoxides in organic synthesis have recently appeared.[‌2‌‌4‌] Organotin oxides are common precursors of organotin alkoxides and also act as very good catalysts for transesterification, esterification, and acetalization reactions. Organotin alkoxides are mainly employed as mild alkoxide sources with strongly nucleophilic properties, but with reduced basicity in alkylation, acylation, or oxidation reactions either in stoichiometric or catalytic amounts. Their reactions occur under mild conditions making them very popular reagents in carbohydrate chemistry. As organotin alkoxides are also easily oxidized under mild conditions, they are valuable intermediates for the conversion of alcohols into carbonyl compounds. The first organotin oxide, 1,1,3,3-tetraethyl-1,3-diiododistannoxane,[‌5‌] was prepared in 1852 and its structure was elucidated shortly thereafter.[‌6‌]

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References


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