Titanium(IV) Isopropoxide-Catalyzed Formation of 1-Substituted Cyclopropanols in the Reaction of Ethylmagnesium Bromide with Methyl Alkanecarboxylates
Oleg G. Kulinkovich*, Sergei V. Sviridov, Dmitry A. Vasilevski
*Department of Organic Chemistry, Belarussian State University, 4, Skariny
av., 220050, Minsk, Belarus, Email: kulinkovich
bsu.by
O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevski, Synthesis, 1991, 234.
DOI: 10.1055/s-1991-26431
Abstract
1-Substituted cyclopropanols are formed in high yields in the titanium(IV)isopropoxide-catalyzed reaction of esters with ethylmagnesium bromide.
see article for more examples
Details
The document details a study on the synthesis of 1-substituted cyclopropanols using titanium(IV) isopropoxide as a catalyst. The reaction involves ethylmagnesium bromide and methyl alkanecarboxylates, yielding high amounts of 1-substituted cyclopropanols. The process is carried out by adding ethylmagnesium bromide in diethyl ether to a solution of esters and catalytic amounts of titanium(IV) isopropoxide at 18-20°C. The mixture is then treated with aqueous sulfuric acid, and the products are extracted and purified. The yields of the products range from 76% to 95%, with specific boiling points and molecular formulas provided for each product. The mechanism involves the formation of an organotitanium intermediate, which transforms into titanacyclopropane derivatives, leading to the final cyclopropanol products. The study references previous works on organomagnesium compounds and transition metal catalysis, highlighting the novelty and efficiency of this method. The document includes detailed experimental procedures, product yields, and spectral data confirming the structures of the synthesized compounds.
Key Words
Kulinkovich Reaction, Cyclopropanols
ID: J66-Y1991-560
