The Reaction between Nitrosyl Chloride and Aryltrimethylstannanes. A New Method of preparing Aromatic Nitroso-compounds

Substituted trimethyl(phenyl)stannanes, XC6H4·SnMe3, react with nitrosyl chloride in methylene chloride at 125 to 0° to give the corresponding nitroso-compounds X6H4·NO. With electron-releasing or weakly electron-withdrawing groups, X, viz. H, o-, m-, or p-Me, o- or p-OMe, p-SMe, and m- or p-SiMe3, yields were in the 50–80% range, but with the electron-withdrawing m-F and o-, m-, and p-Cl substituents they were in the 25–30% range.