Abstract
Lithium diphenylphosphide and arsenide have been investigated as reagents for metal–halogen exchange. Reactions involving two molar equivalents of the anions with 1,2-dibromoethylenes lead to moderate to good yields of acetylenes and smaller yields of phosphorus-containing by-products. Similar reactions with 2,3-dichlorobuta-1,3-diene and 2-chlorobuta-1,3-diene give SN2′ rather than direct substitution products. Evidence is presented that adamantene is an initial product in the reaction of lithium diphenylphosphide with 1,2-di-iodo- and 1,2-dibromo-adamantane, but not with 1,2-dichloroadamantane, although 1- and 2-adamantyldiphenylphosphine oxides are formed in every case. Finally reactions of phosphide anion with geminal dihalides were briefly investigated; 1,1-dibromo-2,2-diphenylethylene gave diphenylacetylene as the major product.
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