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Reacts with 1,2-diols to form 5-membered cyclic dibutylstannoxane derivatives. For use in the glycoside field, see: Synthesis, 409 (1995). Formation of these derivatives is greatly accelerated by microwave irradiation: Synlett, 89 (1994). The stannylene derivatives are activated to electrophilic attack:/n
With bromine, the ɑ-hydroxy ketone is formed: J. Chem. Soc., Perkin 1, 1568 (1979). With acyl or sulfonyl chlorides, overall regioselective monoacylation of the diol at the more substituted hydroxyl can be achieved: Tetrahedron Lett., 21, 221 (1980); J. Chem. Soc., Chem. Commun., 1457 (1985); J. Org. Chem., 55, 5132 (1990); 61, 5257 (1996). Selective monotosylation of 1,2-diols has also been achieved catalytically: Tetrahedron Lett., 41, 3773 (2000)./n
Catalyst for lactonization and lactamization reactions: J. Am. Chem. Soc., 102, 7578 (1980), particularly useful in the formation of macrolides: J. Am. Chem. Soc., 105, 7130 (1983). For catalysis of N-acylation of hydroxy alcohols with microwave irradiation, see: J. Org. Chem., 61, 5264 (1996)./n
Promotes the cycloaddition of Trimethylsilyl azide, L00173 to nitriles to give 5-aryltetrazoles, some of which are important as angiotensin II inhibitors: J. Org. Chem., 58, 4139 (1993):/n
Catalyst for the dehydration of amides to nitriles under neutral conditions: Synthesis, 1724 (1999); for use of microwave irradiation, see: J. Org. Chem., 64, 1713 (1999)./n
For a brief feature on uses of the reagent in synthesis, see: Synlett, 1847 (2004)./n
Hazard Statements: H301-H315-H317-H318-H341-H360-H370-H372
Toxic if swallowed. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye damage. Suspected of causing genetic defects. May damage fertility or the unborn child. Causes damage to organs. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P260-P264b-P270-P272-P280g-P281-P301+P310-P302+P352-P305+P351+P338-P307+P311-P310-P330-P333+P313-P362-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed: Call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant