I. Fleming, E. Thomas
1972
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron
Abstract
Abstract The cyclopropyl chlorides ( 1 and 2 ) rearrange on heating to give stereospecifically the allyl chlorides ( 3 and 4 , respectively). In the presence of nucleophiles such as methoxide ion, the corresponding allyl ethers ( 5 and 6 , respectively) are formed. Analysis of the stereochemistry of these products indicates that they are formed from the corresponding allyl chlorides ( 3 and 4 ), which are evidently the first-formed products of the reaction even in the presence of strong nucleophiles. The reaction of the allyl chlorides ( 3 and 4 ) with sodium phenylthioxide in aprotic non-polar solvents goes predominantly with retention of configuration, but in methanol is normal in giving predominantly inversion of configuration.