1-chlorocyclopropyl phenyl sulfoxides

At first, 1-chlorocyclopropyl phenyl sulfoxide (93) was synthesized from the olefin 92 in three steps in good yield. Treatment of sulfoxide 93 with 2.5 eq of /-PrMgCl in THF at —78 °C for 5 min followed by quenching with CD3OD afforded the deuteriated chlorocy-clopropane (95) in 78% yield with high deuterium incorporation. From this experiment, it was proved that the intermediate of the reaction is a magnesium cyclopropylidene species 94 (equation 26). 

TABLE 4. Synthesis of alkylidenecyclopropanes (118) from 1-chlorocyclopropyl phenyl sulfoxide (116) and a-sulfonyl lithium carbanions through magnesium cyclopropy-Udene (117)... 

Chlorocyclopropyl phenyl sulfoxide undergoes exchange reaction to afford 1-chloro-cyclopropylmagnesium chloride (a magnesium carbenoid) that reacts with A -lithioaryl-amines to give o-cyclopropylarylamines. ... 

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