Organic functional group exchange catalysed by inorganic salts

✍ Scribed by J.A. Miller; M.J. Nunn

• Book ID: 104243448
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 165 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92331-7

✦ Synopsis

Because of steric factors the exchange of a functional group at tertiary saturated carbon is a difficult synthetic operation, often requiring forcing conditions, which encourage side-reactions such as g-elimination. We have discovered that inorganic salt catalysis offers a potentially general solution to this problem and in this paper illustrate our results by describing conditions in which the chlorine of tertiary organic chlorides can be exchanged by iodide ion.

Cur route is based on the well established (Finkelstein) exchange reaction of organic chlorides with iodide ion, using sodim iodide in acetone'. Unfortunately, this exchange fails' for tertiary chlorides , but the directness and convenience of the procedure made it