Merck, 208930-250G, Tin(IV) chloride

General description
Stannic chloride (SnCl4) is a strong Lewis acid widely used as a promoter or catalyst in organic synthesis. It is soluble in most organic solvents.
Application
Stannic chloride can be used to catalyze:
Cyclization of trans β-monocyclohomofarnesic acid to form norambreinolide.
Formation of C-glycosides of aromatic compounds such as thiophene, naphthalene and phloroglucinol trimethyl ether.
Formal [4+2] cycloaddition of 3-ethoxycyclobutanones and allyltrialkylsilanes to form 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones.
Diastereoselective reaction of δ-alkoxyallylstannanes with aldehydes to form 1,5-diol derivatives.

Other applications of SnCl4:
The SnCl4-2,6-dialkoxyphenols complexes can catalyze cyclization of poylenes, such as 4-(homogeranyl)toluene to form trans-fused tricyclic compound.
SnCl4 can act as a promoter during the reaction of ortho-aminobenzonitriles with β-ketoesters and β-enaminonitriles to form 4-aminoquinolines and 4-aminopyridines, respectively.
SnCl4-silver perchlorate forms an effective catalytic system for the stereoselective of glycosylation 1-O-acetyl glucose.