Arenes Disubstituted with Primary Alkyl Groups from Xylylene Dianions

Article abstract of DOI:10.1021/jo00141a027

Xylenes were converted into dianions 1.Reaction of dianions 1 with dialkyl sulfates gave symmetrical dialkylbenzenes 2 (R = R'), while methyl iodide caused oxidative coupling followed by alkylation to give 8.Unsymmetrical dialkylbenzenes 2 (R =/= R') were made by an indirect route involving monoanions 9 and 11.Reactions of dianions 1 with dihalides gave cyclophanes o-3 (n = 5,6,9), m-3 (n = 8-10), and p-3 (n = 9-11) and cyclophanes o-4 (n = 2,5,7,9) and m-4 (n = 2,6,7).Dianion 5 from 2,6-lutidine was used to prepare nitrogen analogues of 2 (R = R') and m-3 (n = 8-10).