A note on three routes to benzyne: decomposition of diphenyliodonium acetate, nitrosation of N-phenylphosphylamidates, and deoxygenation of benzenediazotoluene-p-sulphonate N′-oxide (cupferron tosylate) by phosphorus trichloride

Abstract

Thermolysis of diphenyliodonium acetate in benzene, nitrosation, via p-chlorobenzoyl nitrite, of diethyl and dipheny N-phenylphosphoramidates, ethyl-NN′-diphenylphosphonodiamidate, and NN′N″-triphenylphosphoric triamide, and deoxygenation of benzenediazotoluene-p-sulphonate N′-oxide by phosphorus trichloride all give benzyne in 4–20% yields, by mechanistically similar pathways, as shown by trapping with tetraphenylcyclopentadienone.