Cyclopropanes. XLI. Electron Transfer from Lithium Metal Surfaces to (±) and (−)‐(<i>S</i>)‐1‐Fluoro‐1‐methyl‐2,2‐diphenylcyclopropane

Abstract

Abstract The reaction of (I)‐1‐fluoro‐1‐methyl‐2,2‐diphenylcyclopropane ( 1 ) with lithium metal produced a variety of ring‐opened, as well as cyclopropane, products. Initial electron transfer from the lithium metal surface to 1 is to the phenyl ring of 1 rather than to the carbon‐fluorine bond. Using chiral 1 , the 1‐lithio‐1‐methyl‐2,2‐diphenylcyclopropane produced yielded, upon carbonation, the corresponding acid which was largely racemized. The mechanism of the electron transfer reaction is discussed.