Chloromethylation of cyclopropylbenzene yields a mixture of o- and p-cyclopropylbenzyl chlorides and 1-chloro-1-phenylpropane. Reaction of this mixture with hexamethylenetetramine (Sommelet reaction) gives o- and p-cyclopropylbenzaldhyde and 1-phenylpropan-1-ol. The aldehydes have been separated by g.l.c. and oxidised to o- and p-cyclopropylbenzoic acids.
Iron-Catalyzed Cyclopropanation in 6 M KOH with in Situ Generation of Diazomethane
作者:Bill Morandi、Erick M. Carreira
DOI:10.1126/science.1218781
日期:2012.3.23
simple iron porphyrin complex catalyzes the cyclopropanation of styrenes, enynes, and dienes under the demanding conditions [aqueous 6 molar potassium hydroxide (KOH) solution, open to air] necessary for the in situgeneration of diazomethane from a water-soluble diazald derivative. A biphasic reaction medium arising from the immiscibility of the olefin substrates with water appears essential to the