Catalysis of the cyclohexadienone-phenol rearrangement by a Lewis-acidic clay system

✍ Scribed by Stephane Chalais; Pierre Laszlo; Arthur Mathy

• Book ID: 104218684
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 222 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84602-x

✦ Synopsis

The Few-doped acidic KlO clay accelerates greatly, by factors of 105-106, tbetitle reaction. These rearrangements thus occur in a fewminutes atrocnntenperature, according to [1,21 and [3,31 pathways. FACIIE s-try-allowed pericyclic reactions --such as Diels-Alder cycloadditions, Claisen andCoperearrangeuents-nevertheless require quite bigb reaction tanperatures and/or pressures l-3 .

In that, they are representative; organic reactions are not particularly easy, in an operational 2 sense. Hence, wz have set upan a general program, e.

to refurbish reactions to u&e them yet nxxe inportantto organic chemistry. ~~~boldtbatrationaldesigncan setoptimalreactionconditions

The reactions will bave bigb yields, they will be selective and easily worked-up, they will run at at&ient temperatures and pressures and still they will need only low-cost reagents and catalysts.

We have thus devised solid acidic

4-5

and basic 6-7 catalysts for a nurdxr of organic reactions 2 . For instance, wz have issued a three-part report on catalysis of the Diels-Alder reaction by clays and mxlified clays, acting as cation radical 8, as BrQnsted acidic 2, as Lewis acidic ', or as water reservoir 10 catalysts.