Improved preparative route toward 3-arylcyclopropenes

A convenient preparative protocol for the synthesis of various 3-arylcyclopropenes in a multigram, scale is disclosed. Optimization of the reaction conditions and isolation procedures allowed for significant improvement of the chemical yields of these strained products. The described protocol was used for efficient preparation of a series of 3-methyl-3-arylcyclopropenes possessing different substituents in the aromatic ring. The effect of substitution in the aryl group on the stability of 3-arylcyclopropenes, as well as the corresponding precursors, is discussed. (c) 2008 Elsevier Ltd. All rights reserved.