# Stannoxane

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**Stannoxane** is a [functional group](/source/Functional_group) in [organotin chemistry](/source/Organotin_chemistry) with the connectivity Sn{IV}\sO\sSn^{IV} (IV indicates the [oxidation state](/source/Oxidation_state) of tin). Aside from the oxide group, usually 3 or 4 other substituents are attached to tin. In aqueous or aquatic environments, most organotin compounds contain this group.[1]

## Synthesis and formation

Stannoxanes form upon [hydrolysis](/source/Hydrolysis) of organotin halides. For example, hydrolysis of dibutyltin dichloride gives the tetratin compound (((CH3(CH2)3)2ClSn)2O)2. The hydrolysis appears to proceed via organotin hydroxides. For example, the commercially important [cyhexatin](/source/Cyhexatin) (C6H11)3SnOH converts at 200 °C into the hexacyclohexyldistannoxane:

- 2 (C6H11)3SnOH → ((C6H11)3Sn)2O + H2O

The condensation process is proposed to occur via an [associative mechanism](/source/Associative_mechanism), involving the dimer. Support for this associative mechanism is the finding that Me3SnOH exists in solution as the dimer ((CH3)3Sn)2([μ](/source/Bridging_ligand)\-OH)2.

## Reactivity

Indicative of the lability of the Sn-O bond, **distannoxanes** exchange with other distannoxanes:

- (R3Sn)2O + (R'3Sn)2O → 2 R3SnOSnR'3

The Sn-O-Sn bonds in simple organic derivatives are reactive toward carboxylic acid esters to give unsymmetrical distannoxanes:

- 2 R2SnO + R'CO2R" → R'CO2SnR2\sO\sSnR2OR"

## References

1. Davies, Alwyn George. (2004) Organotin Chemistry, 2nd Edition Weinheim: Wiley-VCH. ISBN 978-3-527-31023-4

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Adapted from the Wikipedia article [Stannoxane](https://en.wikipedia.org/wiki/Stannoxane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Stannoxane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.