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Source of on thermolysis or photolysis of tributylstannyl radicals, avoiding the problems sometimes attributable to the hydrogen donor capability of Tri-n-butyltin hydride, A13298.ɑ-Iodo-ketones or esters with a suitably-placed double bond undergo radical cyclizations on UV irradiation in the presence of a catalytic amount of the distannane: Tetrahedron Lett., 28, 2477 (1987); J. Org. Chem., 54, 1826, 3140 (1989). Compare analogous reductive cyclizations using the tin hydride. Improved conditions have been developed for generation of the tributylstannyl radical by mild UV irradiation in the presence of a triplet sensitizer (e.g. 4'-Methoxyacetophenone, A11162), allowing selective C-C bond forming reactions to be performed under free-radical conditions: Synlett, 287 (1993)./n
Brings about the deoxygenation of amine oxides: Synthesis, 55 (1987), and the photo-desulfurisation of 1,3-dithiole-2-thiones to tetrathiafulvalenes: J. Am. Chem. Soc., 98, 7440 (1976)./n
For reviews of organotin chemistry, see: Tetrahedron, 45, 909 (1989); Synthesis, 259 (1990)./n
Hazard Statements: H301-H312-H315-H319-H372
Toxic if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P280-P301+P310a-P305+P351+P338-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.