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Efficient catalyst for the formation of 1,1-diacetates from aldehydes and acetic anhydride: J. Org. Chem., 62, 1563 (1997)./n
The stereochemistry of the iodolactonization of unsaturated acids to give -lactones can be controlled in some cases. Using I2_-_NaHCO3, the product is under kinetic control, but in acetonitrile, without base, the reaction is reversible and therefore under thermodynamic control. For tabulated results, see: Org. Synth. Coll, 7, 164 (1990):/n
Iodolactamisation of amides can similarly be achieved by prior silylation: J. Org. Chem., 53, 4006 (1988); Org. Synth. Coll., 9, 516 (1998):/n
Secondary, tertiary or benzylic alcohols can be converted directly to the corresponding iodides by simply refluxing with iodine in petroleum ether: Tetrahedron Lett., 36, 609 (1995)./n
Iodine is also a useful mild oxidant, e.g. of aldehydes to acids in alkaline medium: Tetrahedron Lett., 33, 4329 (1992); in DMSO, stilbenes and diaryl acetylenes give benzils: Synthesis, 131 (1991); with hydrogen peroxide, hydroquinones are oxidized to quinones: J. Org. Chem., 54, 718 (1989)./n
For use in the functionalization of remote positions (Barton reaction), see Lead(IV) acetate, A15551./n
For use in hydroboration and reduction reactions, see Sodium borohydride, 35788./n
Hazard Statements: H290-H302-H312-H315-H319-H332-H335-H336-H372
May be corrosive to metals. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation. May cause drowsiness or dizziness. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P234-P260-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P314-P330-P332+P313-P337+P313-P362-P390-P501c
Keep only in original container. 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. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Get medical advice/attention if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant