|Melting point:||183-186° subl.|
Efficient catalyst for the formation of 1,1-diacetates from aldehydes and acetic anhydride: J. Org. Chem., 62, 1563 (1997).
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):
Iodolactamisation of amides can similarly be achieved by prior silylation: J. Org. Chem., 53, 4006 (1988); Org. Synth. Coll., 9, 516 (1998):
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).
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).
For use in the functionalization of remote positions (Barton reaction), see Lead(IV) acetate, A15551.
For use in hydroboration and reduction reactions, see Sodium borohydride, 35788.
|Harmonized Tariff Code:||2801.20|
L201743,5-Dichloro-4-hydroxybenzenesulfonyl chloride, 97%